With the help of the internet and video streaming platforms like YouTube, we have access to more music history than ever before. It can be a gift and a curse—you can watch incredible moments from both the past and present, but there are so many options that it can become overwhelming.
Rappers have been freestyling since the genre's inception, and we know there's no way anyone can watch them all. So we decided to break it down and share some of our favorites in recent memory. Here are 15 freestyles from the 2000s that you have to check out, featuring legends like Clipse, Earl Sweatshirt, Kendrick Lamar, and... Shia LaBeouf.
Mobb Deep's Rap City Freestyle
View this video on YouTube
Year: 2000
Hip-hop lost one of it's greatest warriors and true rebels when Prodigy passed away at age 42. Whether it was alone or as Mobb Deep alongside Havoc, P started when he was 18 years old and made endless contributions to rap even up until his final days.
Back in 2000, Mobb Deep were already well respected as two of the most prolific rappers in the game and had just come off of releasing their platinum album Murda Muzik when they came down to Rap City to spit a hardcore freestyle over the "Get Dealt With" beat from their Hell On Earth album.
Kanye West and Pusha T's Freestyle at Hot 97
View this video on YouTube
Year: 2010
Dressed in all Rosewood attire, Kanye West had arguably his most vulgar interview to date when he stopped by Funk Flex at Hot 97 back in 2010. Ye was gearing up to release My Beautiful Dark Twisted Fantasy and gave Flex an insight to the project by providing funny commentary on topics ranging from potential beef rumors to his nude photos getting leaked. Pusha T was on hand, and to close the interview the two rappers spit a capella freestyles for the New York listeners.
All the fun and jokes were left at the door once the beat dropped. Push and Ye delivered chilling verses that almost sounded better than the final products of "Gorgeous" and "Blow." This was a memorable moment and the perfect close to a press run for one of the most influential rap albums of all time.
Dipset's Rap City Freestyle
View this video on YouTube
Year: 2003
This one was a no-brainer. In 2003, The Diplomats stopped by Rap City and effortlessly made history. Jim Jones, Juelz Santana, and Cam'ron assaulted the Scarface "My Block" production with smooth flows and unforgettable lines. Through their presence it feels like you're watching a day in Harlem and not just a regular freestyle. Jim Jones is wearing a Chiefs jersey and an untied durag under his fitted, Juelz has on his traditional bandana and a jersey of his own, and Cam has on a bucket hat and counts money the entire freestyle. Legendary verses and legendary attire from a group that will live forever in hip-hop history.
Earl Sweatshirt on Sway in the Morning
View this video on YouTube
Year: 2013
By summer 2013, Earl Sweatshirt had already been back from Samoa for over a year and just released his debut album Doris. He missed the entire Odd Future explosion while he was in boarding school and returned to Los Angeles with a fan base larger than he could fathom. When he arrived at Sway In The Morning to talk about his album, you can see that he was still adjusting to the fame and all the changes in his life. Sway played him a beat and Earl delivers a solid freestyle that he immediately declares is "butt."
It's not Earl's most lyrical freestyle, but it is interesting to look back on one of the more wise, elusive artists during a time when he was still developing.
Big Boi and Killer Mike's Rap City Freestyle
View this video on YouTube
Year: 2002
These days, Killer Mike is now known mainly as half of Run The Jewels and for his political voice, but there was a time when he walked into Rap City and killed one of the biggest singles of 2002. Joining Big Boi to promote Speakerboxxx/The Love Below, the then 27-year-old rapper decided to step up to the mic when Big Tigga played 50 Cent's "Wanksta" instrumental.
Killer Mike rapped about everything from his children and Bob Marley to the posters hanging on the walls of the booth. Big Boi followed up with a solid verse of his own but then Killer Mike returns and goes even crazier. Rapping about the stickers on the wall, he delivers bar after bar, finally admitting that they're going to have to cut him off because he's been waiting for this moment his entire life.
Shady 2.0 Cypher at the BET Hip-Hop Awards
View this video on YouTube
Year: 2011
A list of freestyles is void if it doesn't include Eminem. Back in 2011, he was joined onstage by Slaughterhouse and Yelawolf at the BET Awards, and Em delivered one of his more humorous freestyles. Coming off of the release of Recovery, the bestselling album of 2010, Em was working on his next project Bad Vs Evil with Royce da 5'9 and seemed to be on a roll.
All parties involved delivered solid verses, and the biggest moment of the cypher might have come from Royce with his "Hi Rihanna" scheme that was inspired by an interaction he had with the pop star overseas.
Frank Ocean Freestyles with OFWGKTA
View this video on YouTube
Year: 2012
Frank Ocean is elusive to begin with—usually when you do see him, it's a carefully choreographed performance. To see him in an unscripted moment is even rarer. Which makes this Odd Future clip from 2012 all the more valuable, from a time before Frank was constantly hounded by paparazzi. The video clip takes place in Terry Richardson's New York studio and features Frank freestyling while Earl Sweatshirt and company freak out to his punchlines.
Clipse's Rap City Freestyle
View this video on YouTube
Year: 2006
As you can see, a lot of greatness occurred in the booths of BET's hit show Rap City. In 2006, Pusha T and Malice, better known as the Clipse, pulled up to Big Tigga dressed in all BAPE to lay down a freestyle over the "Kingdom Come" beat. Malice kicked things off before Pusha T came in and delivered one of the coldest verses of the year. "Four years of chemistry/You thought it was my misery/I was right at home/Like Merlin with my wizardry," he raps in his signature flow as he glides through what ends up being one of the most popular freestyles in Rap City history.
Kendrick Lamar on Power 106
View this video on YouTube
Year: 2014
In 2014, Kendrick Lamar was riding high off of the success of his major label debut good kid, m.A.A.d city. He had just released his Grammy-award winning single "i" when he appeared on Big Boy's Neighborhood in 2014. The host could not let Kendrick leave without kicking a quick freestyle for the listeners. K.Dot obliged, and went on to spit for a solid five minutes before Big Boy decided to kick some bars of his own. This was a solid effort from the Compton rapper and a look at what was to come after GKMC.
Shia LaBeouf on Sway in the Morning
View this video on YouTube
Year: 2016
You never know what to expect from Shia LaBeouf. When I saw that he laid down a freestyle on Sway In The Morning, I clicked the link thinking that I was going to hear someone stepping out of their lane and having a little fun. I couldn't have been more wrong.
Shia absolutely snapped: he had bars, he took shots, and it was all off of the top of his head. In an era of positivity and bubbly, happy raps I couldn't have been happier to hear someone come through with aggression and cruel intentions. It's a shame that an actor was the guy to do it for me and not an actual rapper but I'll take it. Bravo, Shia.
Lil Wayne's Rap City Freestyle
View this video on YouTube
Year: 2001
Ah, the good ole days.
Long before Lil Wayne and Birdman's relationship went sour, the bond between the two was incredible to watch. Together they released some of the best music of the 2000s and through Birdman's guidance, Weezy went on to become a global superstar. One of the most memorable moments between the two came early in 2001 when Birdman brought a young, hungry Lil Wayne to Rap City to spit for the BET audience.
The Cash Money Records CEO declares, "I'm gonna bet all my money on ya" before making Wayne return to the mic to deliver another impressive verse over the "We Gonna Make It" instrumental. Freestyles ended up being a cornerstone of Lil Wayne's career, and looking back, you can see the potential in him as a rapper as well as the roots of what went on to become one of the closest relationships in hip-hop history.
Donald Glover Freestyles for Peter Rosenberg
View this video on YouTube
Year: 2014
Donald Glover is easily one the most successful entertainers in recent memory, but early on in his rap career as Childish Gambino, he had a chip on his shoulder. Back in 2014 he freestyled over Hit-Boy and HS87’s “Grindin’ My Whole Life” when he stopped by Hot 97's Peter Rosenberg late night broadcast, and he destroyed the beat. Touching on everything from the Los Angeles Clippers to Chance The Rapper, Glover sounded more cynical than ever, and that resulted in some incredible punchlines.
Donald never fit the mold of the traditional rapper, but it's always refreshing hearing him put his lyrical ability on display. He announced that his next release will be the last Childish Gambino album, but let's hope we get a few more freestyles as well.
Kendrick Lamar, Lil B, Yelawolf, and Cyhi the Prince's XXL Freshman Cypher
View this video on YouTube
Year: 2013
Kendrick Lamar is easily one of the biggest names in hip-hop today, but back in 2013 he was a rising prodigy. Kendrick was featured in the XXL Freshman Class that year alongside Travis Scott and fellow TDE member Schoolboy Q. As part of the cover story, XXL has the freshman class freestyle individually and then again in a cypher.
This was Kendrick's moment to shine, as he spit an impressive verse in the cypher that featured Cyhi The Prince, Yelawolf, and a slept-on Lil B verse. This was one of the first, but nowhere near the last time we would see Kendrick Lamar dominate a rap cypher.
Desiigner Freestyles on Flex
View this video on YouTube
Year: 2017
After scrolling through a list of lyrical freestyles, I'm sure readers are wondering how a Desiigner freestyle made it on to the list. Here's why. Of course the 20-year-old rapper delivered his over-the-top energy and outrageous lines as he does every time he appears anywhere, but this situation had a very special moment. What truly makes this freestyle great and the real reason you need to watch is the fact that in the end it sounds like Funk Flex was almost brought to tears after hearing the 20-year-old rapper go off for nearly three minutes.
Desiigner is a legend.
