100 Bold Moves

When you're the most sought after draft pick in the NFL, things tend to go your way. Eli Manning made it clear that he'd never play for the #1 picking-Chargers if drafted by them with little explanation as to why. San Diego still drafted him, only to trade him to New York for Philip Rivers shortly after.

In a sign of the times, the UK division of Sony's record label became the first major to stop using promo CDs, opting for a digital e-card system instead. The development is less costly and more eco-friendly. Expect to see other labels follow suit in the near future.

After loads of late '90s success, the R&B singer was about to set himself up for a flop with the never released LP, All About U. It leaked to negative reception in late 2000, and when its expected 2001 release date came around, the project was canceled. Usher went back into the and returned with the quadruple-platinum 8701 later that year and diamond-selling follow-up Confessions, in 2004.

WiMax is one of those technologies we've been hearing about for years now, but won't take true advantage of until the future. WiMAX is touted as next level Internet with connectivity available pretty much anywhere. It's yet to reach its potential, but creating such an ambitious network is a big step already.

The group Beyoncé got her start with had just landed its first #1 single and everything seemed to be going well. Then, in February 2000, the music video for "Say My Name" debuted and former members LeToya and LaTavia were missing. Instead, newcomers Farrah (later kicked out) and Michelle took their place. The ousted members didn't know of the lineup change until they saw the video on TV and filed a lawsuit immediately after.

Sportscasters had a word for it: "Rocktober." With the help of a last-minute winning streak, the MLB squad barely made the playoffs. Then they went on to upset every playoff opponent before losing to the Red Sox in the World Series. Their dream wasn't entirely fulfilled but it made for a fun ride along the way.

No matter the condition of the music industry, Madge proved that superstars get to play the game differently when she inked a massive $120 million 360 deal with touring giant Live Nation, proving that the power was shifting away from the traditional model of the big four. U2 and Jay-Z would follow in her footsteps, but there's no denying who paved the way.

After planning to end The Oprah Winfrey Show several times, The Big O finally confirmed that she would not be renewing her contract in a September 2009 interview with Diane Sawyer. The show ends in 2011, and Oprah is expected to move into production on her own network afterwards.

Carroll spent every year of the Aughts guiding the USC football team to numerous BCS titles and appearances. However, when offered the Seahawks position, he ditched his decade-long employer and signed up for the big leagues immediately.

LeBron James and the Cavs are always within reach of the NBA championship, and the last-minute trade that landed them Antawn Jamison has made it even more of a possibility. Perhaps a winning Finals appearance is what the franchise needs to keep James from pursuing tenure in New York (or elsewhere) next season.

After a five-year indefinite hiatus, Travis Barker's near-death experience brought the back together and a highly-anticipated reunion tour was immediately in the works. They probably could have sold out venues at ridiculous ticket prices, typical of these types of events, but the band wanted to give everyone a chance to see the show, and sold many tickets for just $20.

In an effort to mobilize youth voters during the 2004 election, Diddy went overboard with Citizen Change's "Vote or Die" t-shirts. The campaign didn't stop Dubya from getting re-elected, but more young people did vote and the spirit was intact by the time Obama showed up and took the 2008 election.

Looking to expand its media conglomerate, Comcast purchased a majority stake in NBC Universal in December 2009 after months of speculation. The deal gave them control of channels like NBC, USA, and Bravo, along with assets like Hulu, Universal Pictures and Universal Studios.

Tiger's talent is so undeniable that it's not even particularly surprising when he wins. The real shocker was when Yang Yong-eun came back from a multiple-stroke deficit in the 91st PGA Championship and upset Tiger Woods to become the first Asian male to take title.

Daniel Dumile was already a mysterious dude and that intensified when fans began alleging that he was not actually performing at live shows, and some magazines claimed that impostors were sent to photoshoots. The claims intrigued some and outraged most, but it's an unheard of ploy no matter how you slice it.

Louie was mostly seen as an accessories line until Marc Jacobs brought his ready-to-wear vision to the fashion house in the late '90s. The brand has seen exponential growth and multiple high-profile collaborations since he was appointed Creative Director, the title he still holds.

Ellen's '90s sitcom was a moderate hit, but ratings were never the same after the episode where Ellen's character came out of the closet. After that, she was given another shot with The Ellen Show in 2001, but that was canceled during the first season. It wasn't until her talk show debuted in 2003 that DeGeneres got back on her feet in Hollywood, proving that an openly gay woman could get down with Middle American soccer moms. Now she's got Academy Awards host and American Idol judge on her resume too.

In response to criticism about their harmful use of plastic, PepsiCo and other major manufacturers of bottled water began widely using a more environment-friendly bottle with 30% less plastic. There's still more to be done, but it's a bold and helpful green initiative.

PC gamers had been playing online for years, but Sega's Dreamcast was the first system to show console gamers what all the hoopla was about. NFL 2K1 was the first game to take advantage of the Internet connectivity, and the industry has never been the same.

"Stay in school" is usually sound advice, but not in the case of Oklahoma Sooners quarterback, Sam Bradford. Dude won the Heisman and broke NCAA touchdown and Oklahoma passing records. He was all-but guaranteed a #1 draft pick when he shocked the sports world and announced that he'd be returning to school for his junior year and passing up the 2009 NFL Draft. Bradford got injured on his first game back. Damn, son.

By September 2009, we'd known Lady Gaga was "different" for a while, but that year's MTV VMAs was like the coming out party for her eccentricity. Arriving with Kermit The Frog, covering herself from head to toe in red lace, a bloody performance, and eventually, bird nest-like headwear may not have earned Gaga best dressed honors. But boldest? Sure.

This 18-player deal between the Minnesota Vikings and Dallas Cowboys is the biggest, boldest, but possibly worst, sports trade of all-time. Cowboys coach Jimmy Johnson wanted to do something drastic to help out the ailing franchise. The Walker trade didn't prove too helpful for the Vikings, but with all the draft pick shifting, the Cowboys wound up getting a little guy by the name of Emmitt Smith and becoming the football team of the '90s.

In the early '90s, HIV and AIDS were still touchy subjects for most of mainstream America. Tom Hanks did his part in creating social awareness about the epidemic when he portrayed a gay lawyer, discriminated against by his own law firm, along with Denzel Washington, his legal representation for the lawsuit. Previously known for comedy, the role ended up earning Hanks top acting Honors at the 1994 Academy Awards and changed the direction of his career forever.

One of rap's youngest stars was mostly known for his breakout 2007 track, "Crank Dat," and widely dismissed as a one-hit wonder until he scored with a string of hits from his sophomore album, iSouljaBoyTellem. The most hating haters couldn't front on "Gucci Bandana" and "Turn My Swag On", and his female fans helped "Kiss Me Thru The Phone" reach #3 on the Billboard Hot 100. His innovative mixtape work is only pointing towards bigger and better things.

The Lakers' acquisition of Pau Gasol is the move that led to the team's 2008 NBA Finals appearance, and 2009 NBA Finals win. All they had to do was give up nobodies like Kwame Brown, Javaris Crittenton, Aaron McKie and draft picks too. What a steal!

Infuriated by Mariah's constant denial of any former romance with the rapper, particularly in her single at the time, "Obsessed", Eminem unleashed all his pent-up frustration about the issue in a summer 2009 diss record, "The Warning." Em described sex with the diva in graphic detail and even lashed out at her hubby, Nick Cannon. Neither half of the couple ever really responded. Some would say they took the high road. We say they were shook.

Heath Ledger's death was untimely and unfortunate, but it did increase interest in his role as the Joker in The Dark Knight. Warner Bros. began to use Joker-imagery more prominently while marketing the film, and it went on to break the record for biggest opening weekend ever with a gross of $158 million. Ledger was posthumously awarded Best Supporting Actor at the following year's Academy Awards.

Before Steve Jobs uttered a single word at the January 2010 Macworld conference, the public already knew to expect a tablet device from Apple. The real shocker came with the announcement of the iPad's introductory price point: $500. The gadget isn't available until April, but it's clear to see how Apple will smash the game, once again, with their newest product going for such an affordable price.

50 Cent and Rick Ross had been sending shots at one another for a few weeks, and when Ross told 50 to "come up with something better" in response to a diss track, Curtis did exactly that. In a viral video released in early February 2009, 50 interviewed Tia, one of Rick Ross's baby mamas, and she confirmed his CO past and fraudulent persona. Then 50 went for the deathblow when he took Tia and a friend shopping. Since then he's dropped "Tia Told Me", which hints at a sexual relationship between the two, and even visited her home with Floyd Mayweather to play with Ross's kids.

Believe it or not, the iPod and iTunes Store weren't always available to everyone. It wasn't until iTunes 4.1, released in October 2003, that PC users got to take full advantage of the groundbreaking MP3 technology. Once that it happened, it was game over for everyone else.

It wasn't enough for Brett Favre to retire and come up short, as he did with the Jets in 2008, just once. He had to go and do it again. As late as July 2009, Favre issued statements that he planned to stay retired. By August, his contract with the Minnesota Vikings was breaking news. It wasn't enough for Brett Favre to retire and come up short, as he did with the Jets in 2008, just once. He had to go and do it again. As late as July 2009, Favre issued statements that he planned to stay retired. By August, his contract with the Minnesota Vikings was breaking news.

The couple played an unlikely love interests on Entourage and turned into the same thing off set. Their relationship only lasted a few months in Fall 2008, but the fact that Turtl-err, Jerry Ferrara even held down Meadow Soprano for that long is a feat in itself.

After leaving USC in 2006, Kiffin bounced around different jobs with less than satisfactory results. His NFL stint resulted in a poor record with the Oakland Raiders and beef with the team's owner, Al Davis. Then he went back to college football for one season with the University of Tennessee in 2009. To everyone's surprise, Kiffin ditched his new squad (and a six-year contract) and headed back to Cali as soon as the head coach position opened up at USC.

What does the best rapper alive do after releasing the highest-selling album, rap or otherwise, of 2008? Why, channel of simple guitar chord sensibilities of late '90s punk rock outfits like Green Day and Blink 182, of course. Wayne took the teen angst angle and added a dose of his own varied rap style, for the semi-awkward, oddly received rock album, Rebirth. Critical reviews were mixed, but the album sold surprisingly given it's lack of promotion and leak one month in advance. Everyone knows Tha Carter IV is the real album to look out for, but Rebirth was a pretty ballsy move to pull off in the meantime.

By March 2008, Guns N Roses' Chinese Democracy was almost 15 years in the making. Dr. Pepper issued the band a challenge: supply each of the 300 million citizens of the USA a free can of their soda if the album hit stores before the end of the year. Their bold strategy worked because it was finally released on November 23. Unfortunately, DP didn't exactly hold up to its end of the bargain. It's website was all but non-functioning on the release date when people when instructed to go there and redeem a free soda voucher.

Ashton's career peaked in the early Aughts, but Twitter, of all things, kept it going strong years down the road. The actor challenged news outlet CNN to a contest to see who could get a million followers first. Kutcher wound up winning in April 2009 and donated his $100,000 winnings to a malaria charity.

You know technology is really changing when the government commissions it. In June 2009, the FCC saw that all analog television signals in the U.S. were ceased and made way for television's digital-only future. Now we get a bunch of free HD channels from the big networks. Double win.

The 2006 NFL Draft had one of the best crops of athletes in recent history. To everyone's surprise, the Houston Texans passed up college stars like Reggie Bush and Vince Young, and went with DE Mario Williams in an effort to improve on defense.

Yeezy was no slouch in the record sales department, but he wasn't moving units like 50 Cent. For a moment, no one was. The pair both released their third albums, Graduation and Curtis, on September 11, 2007. 'Ye ultimately won out, selling almost one million copies in the first week and proving he was hip-hop's new top dog.

Sometimes the saying, "there is no competition," just means that you're better than everyone else. In the case of football gaming, there really is no competition. In December 2004, EA Sports acquired an exclusive license prohibiting any other developers from using NFL teams, players, or stadiums. The contract was recently extended to 2012.

The success of this instantly classic horror flick was bold for a couple of reasons. Not only did director Oren Peli confront for his life-long fear of ghosts while making PA, but he spent just $15,000 in the process. Not bad considering it's made over $100 million. One of the biggest Hollywood success stories, ever.

Sam Raimi's three Tobey Maguire-helmed Spiderman flicks were all insanely successful, but when conflicts arose about the direction to take the fourth film, Columbia Pictures shocked everyone and decided to reboot the franchise with Marc Webb directing and a new, still-unannounced lead for Spidey. The 3D film is set for a 2012 release date.

Although it's been noted that the "Tik Tok" singer had near-perfect SAT scores, school was the last thing on her mind when she dropped out at 17 years old. The Nashville, TN native dipped to L.A. to focus on music and worked menial jobs in to support herself in the meantime. After a few years of getting random work around the music industry, she linked up with Dr. Luke and started making hits. "Tik Tok" stayed at #1 for 9 weeks and broke airplay and digital sales records, and Animal debuted at #1. Her second single is already in the top 10.

Two months were left until the election and the presidential race was heating up. In a last-ditch attempt to win over voters, McCain announced Alaskan governor, Sarah Palin, as his running mate. Of course, Obama won in a landslide victory and Palin never became our vice-president, but it was pretty wild when the news first broke.

When people say, "power is in the hands of the people," these are the types of stories they're talking about. Fox gave Family Guy shifty treatment during its first three seasons, including pitting it against Survivor and Friends, officially cancelling it in 2002. DVD sales and syndicated viewership were so high that the series was renewed and brought back in 2005.

Everybody got a deal, but Drake did it without one. "It" being a number one single, Grammy nods, and sold out shows on the heels of his excellent free mixtape, So Far Gone. The set-up helped Drizzy score of the most lucrative rap contracts ever.

It was a hot July day in Newport, Rhode Island and fans of folk music were eager to see Bob Dylan jam at the Newport Folk Festival. To everyone's surprise and many's dismay, Dylan had abandoned his traditional sound and decided to play electric guitar for the first time. The move alienated some fans, but has ultimately gone down as one of the most significant moments in rock history.

One of the hottest clothing brands in the world saw its popularity increase massively in America when high-profile figures were spotted wearing it. Ever the opportunistic businessman, many believe that BAPE's founder, Nigo, paid Jay-Z and Lil' Wayne $500,000 and $300,000, respectively, to wear the clothes in an MTV interview with Nas and the "Hustler Muzik" video.

A year ago, barely anyone knew who Amber Rose was. Then she started showing up in photos with Kanye, and it was hard to ignore her blonde buzz cut and outrageous style. Since the change, her model resume has gotten a lot deeper and she's just shy of being a household name. What a come-up.

On March 17, 2009, six months before the release of his debut album, Kid Cudi called it quits in a Kanye-like, all caps blog post. He cited music industry drama and vowed to only focus on his acting career after Man On The Moon. Four days later, he "unretired" during a SXSW set. It's been a year, and Cudi is working on his next album, Cudder, and he still has the acting career with a current role on HBO's How To Make It In America.

Mickey D's Dollar Menu debuted in 2002, but it wasn't until the recession hit during the later part of the decade that it really started to pay off. Since the economy's collapsed, McDonald's consistently reported rising profits and outperformed its rivals, even in the face of declining sales. In 2010, they expanded the Breakfast Dollar Menu, hoping to continue fast food domination.

Writers across the country labeled the teen drama "mind-blowingly inappropriate," amongst other criticisms, only to have their quotes flipped and prominently featured in the show's season two ad campaign.

Back in 2006, the wide receiver formerly known as Chad Johnson rocked a jersey bearing "Ochocinco" during warm-ups and was subsequently fined $5,000 for his actions. Three years later, he legally changed his name to Chad Ochocinco, a Spanish interpretation of his number, 85, he but wasn't allowed to play with the new name on his jersey until the 2009 season. Rumor has it, he may change his name to Chad Hachi Go, the name his Japanese fans use, for the 2010 season.

The same year (1996) Calipari won Naismith Coach of the Year, University of Massachusetts's first ever Final Four appearance was vacated when it was discovered that Marcus Camby had accepted $28,000 and gifts from sports agents. John moved on to coach the New Jersey and where he was fined for verbal attacks on sports reporter Dan Garcia and eventually fired after a losing season. The coach saw accolades and wins when he went on to coach at the University of Memphis, but had his best season (2008) vacated after scandal involving Derrick Rose broke. No sweat. Calipari signed an 8-year, $31.65 million contract with the University of Kentucky and this season, they're ranked #1. King.

Khloe was hosting a party for Lamar's teammate, Ron Artest, when the couple met. Exactly one month later, they were husband and wife. Khloe got a pre-nup that groupies die for, and Lamar got a coveted Kardashian. Supposedly, they're really in love, but surely the benefits of mass publicity and a Keeping Up With The Kardashians ratings boost add to the cause. Bold move, either way.

Similar to the Beta vs. VHS battles of the '80s, Blu-Ray and HD-DVD clashed over which technology would secede DVD as the standard home video format. Urban legend has it that VHS beat Betamax because of support from the porn industry. If that's the case, Blu-Ray probably won out because of PS3. Either way, Sony's disc outsold its competitor two to one and the format wars were over by early 2008.

After four platinum-plus albums, the trendsetting musicians turned his sights to the fashion world, with footwear collections for two of the biggest names in the game. The Nike Air Yeezys dropped in three different colorways in April, May, and June of 2009. His Louis Vuitton collection came out that summer. Both ventures performed well and solidified Kanye as someone to reckon with outside the world of music.

In a matter of years, the iTunes Music Store (now just the iTunes Store) went from a niche retailer with a couple hundred thousand items for sale to the world's biggest entertainment store with over 10 billion songs (and plenty of other media) sold.

James Cameron already had the biggest movie ever with Titanic. After 12 years, he topped himself when Avatar broke the two biggest box office records. The film took so long to make because the necessary technology wasn't available when Cameron thought of the idea, and it showed. The movie went on to win three Oscars for cinematography, art direction, and visual effects, with still rising revenues approaching $800 million domestically and $2.6 billion worldwide. Oh, and he has everybody in Hollywood jocking his IMAX 3D steez.

After dealing with varied, if not poor, performance for a while, Ray-Ban sought out the success of its '80s hey-day. When they realized there was still a market for the original Wayfarer, it was re-issued and given placement from many celebs.

Skateboard P already had a stylish reputation when he launched two clothing lines of his own in the mid-Aughts. Although BBC shirts has been circulating for a few years, increased availability, especially during the height of the streetwear-era, made both brands instant hits.

In one of the boldest NFL trades ever, Mike Ditka gave up every one of the Saints' 1999 draft picks (as well as two 2000 picks). The star running back was the draft's fifth pick and a lucrative contract was worked out shortly after.

With the new millenium came a new standard in automobile luxury. Mercedes-Benz and Rolls-Royce upped the ante of amenities with their respective Maybach and Phantom lines. Almost a decade later, and it seems like everyone who considers themselves a baller has snatched at least one of these up.

It was a December night when "You Gotta Love It" and "Swagger Jacker" hit radio and Internet. Even in a pre-Twitter world, everybody was talking about the verbal attack right away. Cam asserted that Jay stole Rocawear and Kanye from Dame, and criticized his age and knack for wearing chancleta sandals. No matter which side you took, the whole thing was wildly entertaining. Cam never got more than a few subliminal jabs from Jay, and Hov's stock has only soared since, but we still commend him to stepping up to the task in the first place.

One year after an embarrassing 24-58 season, everyone playing a role in the Celtics franchise was in the hot seat. After picking up Kevin Garnett and Ray Allen in the offseason, the team went on to win the NBA championship and he best record, 66-16, of the 2007-2008 season. Nice turnaround, boys.

Game's first album is arguably classic, and the 50 Cent hooks and Dr. Dre production have a lot to do with that. After being ousted from G-Unit, Game had support from neither on his second LP. No worries. Doctor's Advocate still debuted at number one on the Billboard charts and eventually reached platinum sales.

The Harry Potter franchise was plenty successful by the time Forbes listed Rowling as a billionaire (claims she later disputed; current estimates put her at $800M), but it wasn't an easy road to riches for the British author. Before the world knew of Hogwarts of other figments of her writing, Rowling was raising a daughter on her own, living on welfare, and saw the original manuscript for Harry Potter rejected 12 times before the franchise caught on. Persistence is key, kids.

Next time you get a crazy movie idea, just remember the only person stopping you from making it is yourself. When Kevin Smith got the bold idea to shoot a comedy about two convenience store clerks, he sold off collectibles from his comic book stash, used insurance money, and maxed out 10 credit cards to make it happen. At a cost of $28,000, Clerks was still incredibly low budget, but grossed over $3 million and jump-started Smith's career as a top filmmaker.

On a September 2004 episode of Oprah, the car company partnered with the talk show host to give away 276 free Pontiac G6s. Sources say the stunt was a hit, increasing web traffic and model awareness immediately.

Instead of going the typical route and starting a social networking with bloated features and photo albums, the Twitter guys kept it simple and changed the game in the process. Jack Dorsey, Evan Williams, and Biz Stone's massively popular site relies on the use of 140-character status updates and has became a haven for endless amounts of news, celebrity drama, and trending topics.

By summer 2008, Rick Ross was a staple on the rap circuit, largely known for flaunting of his past as a major drug dealer. The kingpin claims started to sound a little fraudulent when The Smoking Gun posted documents showing proof that he worked as a corrections officer in a Florida prison in the '90s. Ross initially denied the allegations, but eventually gave in thanks to consistently irrefutable evidence. Bawse?

Tired of searching for music inefficiently, Fanning started the first wildly popular file-sharing service while Boston's Northeastern University. The rose to fame quickly, but the service was shut down by summer 2001, after a series of lawsuits from artists and record labels. Still, two years was more than enough time to change the way we got on hands on music forever.

RDJ is the definition of a Hollywood comeback kid. After portraying a conflicted teen in 1987's Less Than Zero, many of the problems he acted out in the film found their way into his personal life in the late '90s. He was in movies again by 2003, but 2008 was the year Downey really got his swagger back. Iron Man and Tropic Thunder were both summer blockbusters, with his performance in the latter earning him an Oscar nomination for Best Supporting Actor.

After two semesters at Chicago State University, 'Ye hung it up and pursued his dream. The risky but bold decision has inspired his collegiately-themed albums. The move's pay off has been well documented.

The Patriots were destined to have a perfect 19-0 season, until Eli Manning connected with Plaxico Burress for a 17-14 lead with 35 seconds left in the 4th quarter. Manning went on to take MVP honors and the game is largely regarded as one of the biggest upsets in sports history.

The celebrated designer turned around the nearly bankrupt Gucci and Yves Saint Laurent in the '90s. By 2004, he boldly stepped away from his creative director positions at both fashion houses and started his own successful, eponymous line.

In 2003, Nike signed rookie LeBron James for $90 million and Kobe Bryant for $45 million (before a lucrative extension in 2007) and guaranteed itself domination in basketball athletics just as the company had done with Jordan before. Now any level rivalry or companionship between the two is likely to be accentuated by brilliant marketing and products from Nike as well.

The original Star Wars films of the late '70s and '80s had become some of the biggest of all-time and George Lucas continued the trend when prequel, Episode I: The Phantom Menace hit theaters in 1999. Two more installments were released in 2002 and 2005 and box office success remained enormous despite mixed reviews from hardcore fans and critics alike.

In 2000, A-Rod signed the most lucrative sports contract ever with Texas Rangers, for a reported $252 million, but that's old news. The superstar slugger broke his own record with a $275, 10-year contract with the New York Yankees in 2007. The deal paid off when the Yanks won the World Series in 2009, due in part to Rodriguez's outstanding play.

While Brad Pitt and Angelina Jolie were shooting Mr. & Mrs. Smith, his marriage to Jennifer Aniston was falling apart. Aniston filed for divorce in March 2005 and paparazzi pics of Brangelina together popped up less than a month later. The divorce was final by October and Jolie was pregnant by January. Let that marinate for a minute.

Initially a tool just for college students, Facebook opened its doors to everyone in September 2006. The site went on to trump MySpace for social networking supremacy and reach a user base of roughly 700 million people.

Fresh out of a contract with EMI and eager to buck what they referred to as a "decaying business model," Radiohead independently released In Rainbows in digital formats in October 2007. The band let fans pay whatever price they wanted, even $0. The album still made tons of money and debuted at #1 on the Billboard charts when physical copies were released months later.

Lance Armstrong had moderate success as a cyclist earlier in his career, but it seemed like everything would be cut short when he was diagnosed with cancer at the age of 25. After being given chances of survival as low as 40%, Armstrong fought back and began training again as soon as two years after the diagnosis. Then, from 1999 to 2005, he won the Tour de France seven times in a row, a personal and athletic feat few will ever top.

We knew Obama was a political star when he killed his keynote speech at the 2004 Democratic National Convention. Four years later he became our President. The historical race began we he formally announced his bid for candidacy in February 2007.

Even when a show like Seinfeld goes off-air, earnings potential only increases. One year after the series finale, Larry David and Jerry Seinfeld signed a $1.7 billion syndication deal, for which they both received roughly $250 million upfront. The contract's remaining amount and DVD sales alone keep each star raking in around $50 million a year these days.

The show that defined a generation came almost exactly 10 years after it was launched in late 1998. The end of a video countdown that created dozens of superstars signaled a major shift in the way music content is delivered, but MTV has never been one to shy away from change. In 2010, the network removed "Music Television" from its logo.

With artists, especially rappers, flopping left and right in the wake of a peaking download culture, Lil' Wayne proved that good music and a veritable hype machine can work wonders when trying to sell records. The oft-delayed Tha Carter III sold over one million copies its first week and went on to become the top-seller of the year.

Remember when email inboxes were a mess to contain with their measly 4 megabyte storage capacity. If you don't, it's because Gmail set the new standard the day it was released as a beta product in April 2004. Since then, every web-based email client has struggled to keep up, implementing higher storage capacities, chat functionality, and a bevy of other email features pioneered by Google.

What do you do with greatest hockey player of all-time after he helps your team win the Stanley Cup for the fourth time in five years? Most would suggest negotiating a contract extension, for the Edmonton Oilers, the answer was: trade him. The strategy worked once, with the team taking another title in 1990, but the spark fizzled shortly after.

We've all made a million jokes about Kimberly getting smashed out on video, by Ray J of all people, but she's rich and famous because of it. How rich? Well, instead of letting the footage shame her like most other Hollywood starlets, she pulled down $5 million alone from a deal with adult powerhouse Vivid Entertainment to legally distribute the infamous sex tape when she dropped a lawsuit against them. Laugh all you want, Kim's laughing to the bank.

Everyone knows the Kanye West story by now, and it reads like a crash course in bold artist decisions. Sped up soul samples. Popped pink Polo collars. The list goes on, but perhaps the boldest was 808s & Heartbreak, the project that provoked a collective "WTF?" reaction from the hip-hop community when songs began leaking in late 2008. The world's biggest rapper was singing about emotional turmoil, in Auto-Tune, and it came completely out of nowhere (as opposed to The Love Below when Andre 3000 had already been on his weirdo steez for years). Like anything groundbreaking, the LP has its fair share of haters, but it was still wildly successful, and about as bold of a move as you can make.

Apple changed the way we used portable devices once before, with the iPod. In June 2007, they did it again with the introduction of the touchscreen-toting iPhone. Long lines ensued upon its release, and the use of applications and other breakthrough technology was made the phone a huge hit. Three years later, and there's not a phone company on the market that isn't pushing a phone that bites the iPhone in some way.

Jordan was so sick on the day of Game 5 of the NBA Finals that he didn't get out of bed until 3:00 pm, and the the tip-off for the Utah Jazz's home game was at 6:00. The Jazz had just won two games and tied the series at 2-2, and it looked like they might get a third victory when Malone, Stockton, and co. racked up a 16-point lead early in the game. Although visibly affected by the flu, MJ still exploded with 38 points and led the Chicago Bulls to a last-minute victory with a clutch 3-pointer. He's the GOAT.

At the height of the "cola wars" of the '80s, Coca-Cola threw a wrench in the game and completely abandoned its classic flavor out of nowhere. The new taste was poorly received, and the original formula was reintroduced in July 1985, three months after the change. Coke sales were huge for the rest of the year and some people even suggest the entire thing was a marketing gimmick.

Under fire from GLAAD for his sometimes-homophobic lyrics, Eminem was the subject of many protests at the 2001 Grammy Awards ceremonies. In one of the boldest countermoves ever, Em performed a "Stan" duet with openly gay Elton John and silenced critics in the process.

With Leno's primetime ratings suffering, NBC devised a plan to bring him back to familiar territory. This plan required Conan to bump The Tonight Show to 12:05 a.m., essentially the "next-day show", the red-haired fellow refused. Long story short, NBC gave Tonight back to Leno; Conan and staff got a $45 million severance package. Only time will tell if it was a smart move, but Late Night TV will definitely never be the same.

With one remaining album under with Def Jam, Hov bought out his contract and started the Roc Nation imprint in a $150 million deal with Live Nation, the first time a superstar rapper had opted out of the traditional industry framework. He didn't get dropped. He dropped the label.

Chappelle's Show was just about the biggest and best show in the world, when Dave Chappelle walked out on production in May 2005 and sought refuge in South Africa. He didn't like the direction the controversial show was going, and turned down a $55 million contract for the third and fourth seasons. Dave and his family now reside in the quiet town of Yellow Springs, OH.