Every Year of Leonardo DiCaprio's Life, Ranked

Image via Complex Original

Turns: 29

Big moment: Is there one?

What a rough year for our young hero. He was still riding on the success of Catch Me If You Can and Gangs of New York, but with only The Aviator to work on and nary a girlfriend to hold him down, Leo's creepier, lamer tendencies came to the fore. He reportedly rigged a game of strip poker to get Natalie Denning naked; he told Globe magazine, “I'm obsessed with girls. When you're my age, your hormones are just kicking in and there's not much besides sex on your mind”; he reportedly lost a potential hookup to another member of the Pussy Posse , and even Daniel Baldwin said he was going to kick his ass. Yikes. By the end of the year, Leo was back together with Gisele Bundchen, but the damage had already been done. It was, in fact, the worst of times. —Andrew Gruttadaro

Turns: 37

Big moment: Right after splitting up with Bar Rafaeli for good, he dates and dumps Blake Lively.

Once again, many fans thought DiCaprio would be a shoe-in for an Oscar for his work in J. Edgar as the titular character. The Academy loves biopics, especially biopics about the possibility that the first director of the FBI may have been closeted. Unfortunately, despite Dicaprio’s dedicated performance, the film bricked. —Tara Aquino

Turns: 6

Big moment: Leo's father pressures him to lose his virginity.

When Leo was 6, his father, a comic book trader-cum-artist, told him to try losing his virginity. What parents tells their six-year-old to have sex? This was also around the time DiCaprio killed a pigeon, thereby scarring him for life. These were trying times. —Hope Schreiber

Turns: 27

Big moment: Don's Plum gets a European release.

Things were looking more than a little shaky for our dear prince in 2001. Following Danny Boyle's creatively uneven The Beach, it seemed possible that Leo mania could be ending. The year's only release (if you can call it that) was the European distribution of Don's Plum, the Pussy Posse vehicle that was originally filmed in the mid-'90s and canned for fear of destroying DiCaprio's image. While it never saw theaters in the U.S., the film was still a big success overseas due to its home video-style look and star power. So even in an off year, Leo invented mumblecore? —Nathan Reese

Turns: 32

Big moment: Gisele and Leo split for the last time.

This year, Leo broke up with Gisele Bundchen for good. For the first time in his life, there's a suggestion that he might be fading—he might not be that Don Juan guy anymore. And when her publicist suggested she hook up with him, here's how Mischa Barton said she responded: “Isn't Leo, like, 30 or something?” Sure, Mischa was at the height of her career in 2005, but still, ouch. Year 31 was a definitely a year in which Leo had to look himself in the mirror and decide whether or not he was going to step up. Just ask 2006 and Bar Refaeli if he did. —Andrew Gruttadaro

Turns: 25

Big moment: Leo battles defamation attacks from Thai protesters while filming The Beach.

Not the strongest year for Leo’s public image. In March, a Time feature detailed the making of The Beach, Leo’s first big movie as a headliner. The article’s most interesting bits focused on how much the people of Thailand hate Leo. In their eyes, he and The Beach’s whole production had damaged the Khao Yai National Park and its surrounding areas during filming, leading ambitious haters to stage protests in which they wore “Leo masks decorated with fangs dripping blood.” Then, in April, the parents of kids killed in a Kentucky high school shooting spree blamed, among other pop culture things, Leo’s film The Basketball Diaries for influencing the shooter. 

It wasn’t all terrible in 1999, though. In addition to dodging a potential worst-idea-ever bullet by not starring a fourth Godfather movie, Leo did what he does best—he began dating one of his (probably) thousands of beautiful women (Britain’s Got Talent contestant Francine Lewis). Even in his darkest days, Leo always finds the light. —Matt Barone

Turns: 10

Big moment: Leo gets denied by a prospective talent agency.

Barely into two-digit life, Leo already knew his calling, but a talent agency didn't share the same foresight, turning him down because he “didn't have the right haircut.” A sobering pre-teen lesson, which to be honest, most people get blows to their self-esteem at age 10. Except nobody else grew up to be model-dating Dicaprio.  —Hope Schreiber

Turns: 5

Big moment: Leo is removed from the set of Romper Room.

Being fired is tough, but imagine being fired at the age of 5. DiCaprio was on the set of the children's educational program, Romper Room, when his behavior forced producers to give him his first pink slip. —Hope Schreiber

Turns: 11

Big moment: Leo catches the perfect frog, and makes it his best friend. Probably.

Ten years from now Leo will turn down the role of Robin in Batman Forever (good call, Leo). At the moment, though, he's going frog hunting in Malibu. You can't go frog hunting in Malibu anymore. They've all been wiped out by polution. The budding environmentalist is on his way to becoming a thorn in the side of every global warming denier in America (we're guessing here). It's also around this time that Leo got his ass beat by some tough kids on the playground blacktop. He stole their basketball, so they retaliated by jumping him and tying his shoelaces together. —Lauretta Charlton

Turns: 33

Big moment: Leo produces The 11th Hour.

2007 saw the beginning of DiCaprio's Clooneyfication, a process every playboy must undergo in order to age gracefully. This can occur in many forms—Matt Damon's fracking forray is an example of another rocky start to this process—but it's fact is a near inevitability in H-wood. Though Blood Diamond was a message movie in its way, DiCaprio's production credit on The 11th Hour, a less talked about Inconvenient Truth, is a more realized version of the transformation. Unfortunately, the well-intentioned climate doc's reception proved to be an inconvenient truth (or lack thereof) for our boy Leo. Only now, in 2014, is Leo beginning to approach The Full Clooney. —Nathan Reese

Turns: 1

Big moment: Leo deals with his parents' divorce.

In 1975, Baby Leo was just starting to say his first words, which, if you think about it, is the first steps to memorizing the powerful soliloquies from Romeo and Juliet. This was also around the time Leo supposedly dated his first model, the Gerber baby. But who could trust gossiping infants? —Hope Schreiber

Turns: 8

Big moment: Leo notices a holy light shine on hair products.

On March 9, 1982, all the planets aligned on the same side of the Sun. It was a rarity, and for some it may have seemed bizarre. Even more bizarre? The light chose to shine in a single place for eight uninterrupted moments on Earth, and no where else. It was exactly where Leonardo DiCaprio was standing, and the moment he realized hair gel really gives his hair a certain je ne sais quoi. (Or we just made that up.) —Hope Schreiber

Turns: 18

Big moments: He turns down Hocus Pocus.

First, the bad. Our boy turned down the lead role in Hocus Pocus. Obviously it all worked out—Leo was holding out in hopes of landing a role in a little movie called What's Eating Gilbert Grape and no one at the New York Times was tripping over themselves to profile Omri Katz. (Imagine if the god had been the one to light the black flame candle.) In other real-actor news, LDC got handpicked by Lord De Niro to star alongside him in the film adaptation of Tobias Wolff's A1 memoir This Boy's Life.

The future was right there in Leo's first interview ever, a chat with a reporter doing profiles for This Boy's Life. SSD: "Good luck becoming a big star." LDC: "Who knows? It could or could not happen. It’s one of those things. But hopefully I’ll be an actor, which is what I’m most concerned about. Not a star." He's not a star. Somebody lied. Leo is MMG. —Frazier Tharpe

Turns: 35

Big moments: Leo deals with heartbreak by planning to build an eco-resort on the island he owns off the mainland of Belize, which he bought in 2005.

2009 was a tough year for ladies’ man Leo. He and Bar Refaeli to a break for six months, starting in June. Was it because he needed to spread his wings for a summer fling? Was it because he realized how weird it was to say “Bar” during coitus? In early 2010, they got back together for one last go, but the “Bar” thing probably was still weird. —Tara Aquino

Turns: 15

Big moment: He stars in The New Lassie.

Did we need a new Lassie in 1989? No, but that's beside the point—because Leo is on the come-up and needs work. Hence, a small role in the Lassie reboot, cleverly named The New Lassie, which aired from 1989 to 1992. Leo appeared in the first season, during the 10th episode, riding a BMX Bike on team Glen Ridge Riders. Hardcore. If you can handle the Polish overdub, you can watch him and his out-of-control, perfectly coiffed blond hair on the YouTubes. Behold. —Lauretta Charlton

Turns: 34

Big moment: Body of Lies and Revolutionary Road open to mixed receptions.

Any sleeper year for Leo could be another actor's crowning achievement—case in point: 2008. While the 34-year-old saw the release of both Revolutionary Road and Body of Lies, neither developed into a full-on sensation. Still, Road was a solid prestige pic netting bestie Kate Winslet an Oscar nomination. Body of Lies, on the other hand, was a Ridley Scott miscalculation that marks one of latter-day Leo's few missteps. Don't worry, bud Brad knows how you feel.—Nathan Reese

Turns: 4

Big moment: DiCaprio starts to woo the ladies.

In an important display of foresight, Leo vowed to never be a sore loser. After losing a three-legged race alongside his childhood best friend, he shook the winners' hands while his friend sobbed in the dirt. He told parents, “It's just a ribbon. I do three-legged races because it's what I love to do, and I love the people I work with. I don't do it for the recognition.” (Probably.) —Hope Schreiber

Turns: 2

Big moment: An eagle picks DiCaprio up and flies him around before dropping him softly in a nest of American flags. It caws three words before it flies away, “Great. American. Actor.” At least, rumor has it.

America's Bicentennial. The 200th anniversary of the Declaration of Independence. The second year of Leonardo DiCaprio's life. Coincidence? Well, why don't we ask our forefathers, namely one John Adams. On his death bed, on the fourth of July, 1826, Adams shared his last words, “Leonardo lives.” (Citation needed.) —Hope Schreiber

Turns: 7

Big moment: Leo figures out his carbon footprint.

At the age of 7, while most children are perfecting reading skills and working on social development, Leo became more worried about the world's development—as in, humans negatively impacting the planet's development. After witnessing numerous women using hairspray to perfect large '80s up-dos, he discovered the connection between aerosol spray and the hole in the ozone layer. (Unless some jokester edited the Wikipedia about the scientist who actually discovered this?) —Hope Schreiber

Turns: 3

Big moment: Leonardo learns to zip his own jacket and make a perfect dry martini. Reportedly.

Potty training is introduced. DiCaprio told his mother he only wore diapers because he was “researching a role of a man slowly succumbing to age, while his children have to learn to take care of the father that always took care of them,” but she suspected he was actually afraid of the toilet flushing. That probably didn't happen. But it could have. —Hope Schreiber

Turns: 9

Big moment: DiCaprio falls in love with Robert De Niro, De Faro, De Wherever-you-are-o.

When Leo was 9, his father took him to the movies to see Midnight Run to show his son what a great actor looks like in Robert De Niro. The star has said that he has modeled his career after De Niro's ever since. —Hope Schreiber 

Turns: 12

Big moment: Leo wisely refuses to change his name to Lenny Williams.

“Leo sniffing glue, he was 12 years old.” Just kidding! Those are (basically) the opening lines of Jim Carroll's song “People Who Died.” Carroll, of course, wrote The Basketball Diaries, which was adapted for the screen in 1995 and starred a strapping young Leo. So, what was Leo actually doing when he was 12? This was the year he decided he wanted to take acting seriously, but struggled to find an agent because he refused to “anglicize his name” to Lenny Williams. Glad he didn't do that. —Lauretta Charlton

Turns: 14

Big moment: Leo goes commercial.

You have to crawl before you ball, and at this time in young Leo's life he was crawling out of the muck that is auditioning for and acting in lame commercials. Matchbox and Bubble Yum are the two most notable ones he filmed in 1988. It's important to note what incredible elocution Leo has in that Bubble Yum gig, though. Nice job, young Wilhelm. —Lauretta Charlton

Turns: 13

Big moment: Leo and Tobey Maguire become buds.

Andy Warhol died this year. Andy Warhol was good friends with Lou Reed of the Velvet Underground. Lou Reed and Leo's father, George DiCaprio (a.k.a. “the Zelig of the counterculture”) were friends. You'd think there would be no connection between the young child actor and one of the greatest contemporary artists of all time, but you're wrong. It's there. Also, Leo met lifelong BFF Tobey Maguire, which has nothing to do with Lou Reed, but is also a very big deal. —Lauretta Charlton

Turns: 20

Big moment: Leo appears on Leno for What's Eating Gilbert Grape, but loses the Oscar for the film.

The first of many Oscar Ls to come was taken this year for What's Eating Gilbert Grape. But there's no cause to scream internally when you're barely 20, on your second major film, and already up against veteran dinosaurs like Tommy Lee Jones and murdering an already-star like Johnny Depp on his own shit. An appearance on Leno—where the god explains his name originates from kicking around his mother's stomach while his parents were looking upon da Vinci works—predicted it all: “He's gonna be a big star.” Hell of a way to close the book on the teen years. —Frazier Tharpe

Turns: 26

Big moment: Leos interviews President Bill Clinton about saving Earth from pollution.

First, the year kicked off disastrously, with The Beach—the first film Leo shot after Titanic’s gargantuan release, and his first look as an official leading man—earning a scant $15 million during its opening weekend, only to reach $39 mil in the States.

A week after The Beach’s opened, Leo graced the cover of Time and gave an awkward, somewhat paranoid interview in which he says “dawg” often (“This is T-I-M-E, dawg!”), listens to A Tribe Called Quest, has the reporter pay for his $155 worth of groceries, and later faxes the writer to make sure he emphasizes Earth Day 2000 chairperson Leo’s belief that “the carbon dioxide in the Earth’s atmosphere is having disastrous and irreparable effects on our climate.” A month later, Leo, via ABC News, scored a 15-minute interview with President Bill Clinton to further push his save-the-planet agenda. Leo talked to Slick Willie about how people need to “give up their SUV’s,” but, as a Slate article pointed out, their interview only happened because ABC News manipulated the White House’s gatekeepers.

For not calling President Clinton “dawg,” though, Leo deserves props. —Matt Barone

Turns: 16

Big moment: Leo gets his first starring gig on Parenthood. 

Like for most people, turning 16 was a huge transition point for Leo. He got his first starring gig as Garry Buckman on 12 episodes of Parenthood, but more importantly, he competed on Fun House, a Double Dare-like game show in which Leo took exploding “shmutz boms” to the chest, went bobbing for plastic fish, and ran his fingers through his hair seductively. And in the process, he forcibly introduced several girls in the audience to the concept of sexual desire. Speaking of, Russell Crowe famously said that an 18-year-old Leo admitted to being a virgin on the set of The Quick and the Dead, to which Leo responded, “He has no idea what he's talking about.” Is that because Leo dropped that V-card in 1990? —Andrew Gruttadaro

Turns: 38

Big moment: Leo walks Kate Winslet down the aisle at her wedding with Ned Rocknroll.

For his work as the villain, Calvin Candie, in Django Unchained, Leo earned his ninth Golden Globe nomination. His batshit insane performance reminded people that he’s not all hype—dude's got immeasurable talent. Off screen, Leo split with model girlfriend No. 39,398, Erin Heatheron, whom he dated from Dec. 2011 to Nov. 2012. But mostly people remember Django.—Tara Aquino

Turns: 30

Big moment: The Aviator continues Scorsese's love affair with Leo.

The Aviator was Leo's second collaboration with Martin Scorsese, and an even bigger boost to his career than Gangs of New York. For one, he carried the entire film, playing Howard Hughes as he aged from a young genius to paranoid recluse with immersive believability—not an easy task for a 29-year-old. (They both suffered from OCD—how method is that?) For another, making a Howard Hughes film had always been a dream of DiCaprio's, so it was a huge win for him personally as well as professionally. The only black mark was that it lead to yet another Oscar snub, something that DiCaprio would only get more used to as the years went by. —Nathan Reese

Turns: 40

Big moment: Leo raps "Scenario" with Jamie Foxx at Richie Akiva's birthday party at 1OAK. 

2014 had been lived the way anyone hit with the realization that they're about to turn 40 would. First, Leo kicked off his 39th year by partying in New York City with American royalty, Kim and Kanye, and then started dating model Toni Garrn. Laughing in the face of maturity, dude made partying his mantra, even attending Robin Thicke's divorce bash. But, lest you forget, Leo's as much of a social justice crusader as he is a socialite, exemplified when he was appointed as the UN representative for climate change. Around this time, he also apparently wore a monkey mask to escort women into a car after a Halloween party. Maybe he feels a deep connection with monkeys, because he also produced Virunga, a documentary that follows people risking their lives to save the last mountain gorillas while civil war occurs in Congo. —Tara Aquino

Turns: 36

Big moment: Two of his films, Shutter Island and Inception, gross over $250 million worldwide.

Shutter Island came out this year, but it will forever live in the shadow of DiCaprio’s shining 2010 moment, Inception. Four years later, fans are still dissecting the plot and praising Leo’s performance. He not only rekindled a relationship with Bar Refaeli during this year, but he also melted the coldest heart in all of mother Russia, President Vladimir Vladimirovich Putin. DiCaprio earned his respect when donated $1 million to Russia's tiger summit to help protect the animals, even though he arrived to the summit, a day late, because of flight delays.

Also, throwback to 2005, when Leo was hit in the face with a bottle by model Aretha Wilson. In 2010, she pleaded guilty and was sentenced to two years for the violent attack. —Tara Aquino

Turns: 0

Big moment: Leo sleeps through the night like a big boy.

A star is born. Figuratively. —Hope Schreiber

Turns: 17

Big moment: Leo stars in Critters 3, his first film role.

At the age when your average 17-year-old is sitting pretty as a high-school senior, the young Cap hedged his bets as a Hollywood freshman, taking his first film role in the modest, direct-to-video (gasp!) Critters 3, then heading back to school for a notable recurring spot on Growing Pains. Just two year, later he'd awesomely dismiss his Critters role as “your average, no-depth, standard kid with blond hair.” Still, it accomplished all that it needed to: the future prince's foot was firmly in the door. —Frazier Tharpe

Turns: 24

Big moment: "Leo, Prince of the City" is published.

This was the year Leonardo DiCaprio officially became “Leo.” Riding the success of Titanic, DiCaprio was living the high life as he traversed the world with his infamous Pussy Posse. (Members included David Blaine, Harmony Korine, Lukas Haas, and Leo's BFF Tobey Maguire.) Chronicled by the classic Nancy Jo Sales' New York magazine story “Leo, Prince of the City,” DiCaprio's exploits are now legendary, but at the time he was just doing what any millionaire playboy in his early-20s would do: get as much, you know, as possible. Not even a Golden Raspberry for his portrayal of twins in The Man in the Iron Mask could slow him down. —Nathan Reese

Turns: 21

Big moment: The Basketball Diaries, The Quick and the Dead, and Total Eclipse are released.

Can you believe studios were still fronting on our boy even in the wake of bangers like This Boy's Life and Gilbert Grape? Sony apparently wasn't sold when casting for Sam Raimi's The Quick and the Dead, but Sharon Stone was—so much so that she fronted Leo's salary. The A-list co-signs just kept coming, and LDC didn't waste them, exercising his penchant for superior role selection early with attention-grabbing, “fearless” turns in The Basketball Diaries and Total Eclipse. —Frazier Tharpe

Turns: 22

Big moment: Romeo + Julie brings Leo alt infamy.

Titanic may have marked peak DiCaprio in 1997, in terms of Tiger Beat fangirl status, but the year before made Leo an art-kid heartthrob with Baz Luhrmann's glam, glitter, and gun-filled Romeo + Juliet. (The plus symbol is key, because '90s.) Leo also flexed his acting chops opposite Meryl Streep, Diane Keaton, and Robert De Niro in Marvin's Room, a film whose ridiculous cast is weirdly disproportionate to how little we talk it about these days. —Nathan Reese

Turns: 19

Big moment: What's Eating Gilbert Grape gets Leo his first Oscar nom.

We don't even need to talk about What's Eating Gilbert Grape—1993 would have still been incredibly dope without that Best Supporting Actor nom. Know why? Because with the Pussy Posse starting to gain steam, Leo scooped up “Cherry Pie” video vixen Bobbie Brown and made rock 'n' roll sex god Tommy Lee look like an amateur. I'll let Brown explain: “I knew him from the clubs, he was always coming up to me saying, 'You're going to be my girlfriend one day.'” Fucking awesome. And then: “We went back to his place that night. He turned on some music and started singing the TLC song 'Waterfalls' to me.” Fucking awesome, part two. Finally: “When I pulled his pants down I was like, 'Holy shit.' I'd just been with Tommy Lee, but Leo looked huge.” Kid was a legend before his 20th birthday. —Andrew Gruttadaro

Turns: 32

Big moment: The Departed puts Leo back on the map.

In 2006, we learned that Leo's hand does not shake. Ever. And neither does his career. Following 2005's rocky break-up (we assume) with Gisele, DiCaprio was back on top with two massive projects—Martin Scorsese's The Departed and Ed Zwick's underrated Blood Diamond. While the latter was more bling bang than bling bling at the box office, his role as a rakish diamond smuggler still managed to earn him a third Oscar nom. But it was the The Departed, a massive sensation both critically and commercially, that put the year over the edge. Dude was everywhere. —Nathan Reese

Turns: 39

Big moment: The Great Gatsby and The Wolf of Wall Street hit theaters.

2013 was the year Leo got back on top of the world playing two fallen-from-grace rich dudes in The Wolf of Wall Street and The Great Gatsby. However, it was the former that captured the zeitgeist with a Quaaludes scene that'll be immortalized in listicles so long as the Internet is alive. More than becoming every Entourage fanboy's wet dream, Leo also made sure to remind people he's not the asshole he's worshipped for playing. In April 2013, he donated $61,000 to GLAAD, an organization which promotes the image of LGBT people in the media. —​Tara Aquino

Turns: 28

Big moment: Catch Me If You Can and Gangs of New York drop less than a week apart.

Leo arguably reaches god level in 2002. His two movies this year, Catch Me If You Can and Gangs of New York, are directed by cinema's two biggest giants currently working, Steven Spielberg and Marty Scorsese, respectively; they drop five days apart in December and gross close to $110 million combined in the first week. This may also be the year that Leo became the shut-away, somewhat mysterious actor we know now. After a post-Titanic lull in which more people talked about his relationship with Gisele than The Beach, Leo basically turned his middle finger up at the public and stopped giving a fuck about what people thought—and how much attention they were giving him. Just read this interview he did with the New York Times, in which Leo beats the shit out of the writer in a game of ping pong, like a G.

Sure, he stopped getting it from Gisele Bundchen in 2002, but something tells me he was getting his needs met elsewhere. Case in point: at the time he was rumored to be hooking up with Nicole Kidman and Cameron Diaz, among others. God. Level. —Andrew Gruttadaro

Turns: 23

Big moment: Titanic.

Until Leo finally wins the Oscar that's been ripped from his deserving hands time after time, Titanic will remain the highlight of his long, varied career. That may not be how he sees it (nor what he deserves), but it's a fact as true as Leo's love for supermodels and the south of France. (He prefers Èze.)

He'd been semi-famous for years, but it was James Cameron's disaster movie that made Leo a household name and elevated him to Hollywood royalty. Before Titanic, Leonardo Wilhelm DiCaprio was just a child actor with an ungainly name. After, he was Leo: a young man with his photo plastered in tween girls' bedrooms from Toronto to Tokyo. Our Prince of the City become King of the World. —Nathan Reese