We Ranked Every Year of Leonardo DiCaprio's Life So Far

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 (UNFORGIVABLE), 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

Year: 2011

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 shoo-in for an Oscar for his work in J. Edgar as—get this—J. Edgar. The Academy loves biopics, especially biopics about the possibility that the first director of the FBI may have been closeted. Unfortunately, despite DiCaprio’s performance, the film bricked. -—Tara Aquino

Turns: 6

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

When Leo was six, his father, a comic book trader-cum-artist, told him to try losing his virginity. What parent tells their six-year-old to have sex? This was also around the time DiCaprio killed a pigeon, thereby scarring him for life. Dark. —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: 31

Big moment: Gisele and Leo split for the last time

After splitting from Gisele, for the first time in Leo's 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 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 Rafaeli 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 activists to stage protests and wear “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 in a fourth Godfather movie, Leo did what he does best—he bagged 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 learns about rejection

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 on the bullshit practices of Hollywood almost made him quit altogether. That agent probably manages reality TV “writers” now. —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 five. 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: 41

Big moment: It's not great, but this Drudge headline: "DICAPRIO RAPED BY BEAR IN FOX MOVIE"

Kind of weak year for Leo, relatively speaking. Reshoots on The Revenant, which would come out late in 2015, were going terribly. And besides that, it must have been so annoying to crawl through mud for hours on end just so Alejandro González Iñáritu could get the shot right. AND THEN, just when Leo's probably thinking the stress of The Revenant shoot is over, and he can lay back and wait for the acclaim, stupid Matt Drudge comes along and tells everyone that Leo was bear-raped. Bear-rape allegations are not fun for the victim, though they are outrageous fun for the viewing public, so that ends up being the noisiest moment of Leo's 2015. Regrettable. Also regrettable? The dissolution of Leo's relationship with Kelly Rohrbach, then a very good looking model who is now a very good looking actress. But no matter how rough Leo's year was in 2015, we're sure he was willing to slog through it, because he knew he was on his way to the promise land. —Andrew Gruttadaro

Turns: 11

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

Ten years from 1995, Leo will turn down the role of Robin in Batman Forever (good call, Leo). In 1985 though, he's going frog hunting in Malibu. You can't go frog hunting in Malibu anymore. They've all been wiped out by pollution. 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 a 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. —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 step to memorizing the powerful soliloquies from Romeo and Juliet. This was also around the time Leo dated his first model, the Gerber baby. At least that's what I'm told—but who could trust gossiping infants? —Hope Schreiber

Turns: 8

Big moment: A holy light desends upon Leo and shines 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. (Probably.) —Hope Schreiber

Turns: 35

Big moment: Leo deals with heartbreak by building an eco-resort on an island off the mainland of Belize

2009 was a tough year for ladies’ man Leo. He and Bar Refaeli split up 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, but the “Bar” thing probably was still weird (they split in 2011). —Tara Aquino

Turns: 15

Big moment: Leo stars in The New Lassie

Did we need a new Lassie movie 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—just look at 2008. While DiCaprio's thirty-fourth year 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 nom. 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 cawed three words before it flew away: “Great. American. Actor.”

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 seven, 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 effecting the planet's development. After witnessing numerous women using hairspray to perfect their large '80s up-dos, he discovered the connection between aerosol spray and the hole in the ozone layer. (Unless some jokester on Wikipedia lied?) —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 nine, his father took him to the movies to see Midnight Run to show his son what a great actor looks like: Robert De Niro. Leo has since said that he has modeled his career after De Niro's. —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 to film in 1995 and starred the 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. Aside from Lenny Bruce and Lenny Kravitz, Lenny is a horrible name. —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. Ads for 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. Truly howing lots of promise, young Wilhelm. —Lauretta Chalton

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 Gilbert Grape; loses the Oscar race

The first of many Oscar Ls to come was taken this year. But there's no cause to scream internally when you're barely 20, on your second major film look, and already up against veteran dinosaurs like Tommy Lee Jones and basically murdering an already-star like Johnny Depp on his own shit. An appearance on Leno—where the god explains that his name originates from kicking around his mother's stomach while his parents were looking upon da Vinci artwork—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: Leo interviews President Bill Clinton about saving Earth from pollution

The year began 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, eventually reaching $39 mil in the states and only recouping its $50 mil budget overseas.

A week after The Beach’s opening, Leo graces the cover of Time and gives 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, scores a 15-minute interview with President Bill Clinton to further push his save-the-planet agenda. Leo talks to Slick Willie about how people need to “give up their SUV’s,” but, as a Slate article points 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 role

Like most people, Year 16 was a huge transition year 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, forcibly introducing 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 Year 16? —Andrew Gruttadaro

Turns: 38

Big moment: Walking 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 Heatherton, whom he dated from Dec. 2011 to Nov. 2012. —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 a paranoid recluse with total believability—not an easy task for a 29-year-old. 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 led 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: Rapping "Scenario" with Jamie Foxx at Richie Akiva's birthday party

Leo's 2014 was lived the way anyone hit with the realization that they're about to turn 40 would be. First, Leo kicked off his 39th year by partying in New York City with American royalty, Kim and Kanye. Then he 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 by his appointment as a 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, that of Vladimir Putin. DiCaprio earned his respect when he 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 plead guilty and was sentenced to two years for the violent attack. —Tara Aquino

Turns: 0

Big moment: Sleeping through the night like a big boy

In 1974, Leonardo DiCaprio was chosen for the role he was born to play—newborn. While only mere seconds old, he proves himself to be a natural, though 1974 also marks the first year DiCaprio was snubbed by the Academy. —Hope Schreiber

Turns: 17

Big moment: Dude was in Critters 3! It was his first movie!

While 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. He then headed back to school for a notable recurring spot on Growing Pains. Just two years 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 and with that, the Pussy Posse is born

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 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-twenties would do: get as much… you know, as possible. Not even a Golden Raspberry for his portrayal as 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 all released

Can you believe studios were still fronting on the 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: 21

Big moment: Romeo + Julie brings Leo alt infamy.

Titanic may have marked peak Leo in terms of Tiger Beat fangirl status in 1997, 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.) The same year, Leo flexed his acting chops further opposite Meryl Street, Diane Keaton, and Robert De Niro in Marvin's Room, a film whose ridiculous cast is weirdly disproportionate to how little we talk about it 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 twentieth 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, 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 movies Catch Me If You Can and Gangs of New York 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 also 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 and 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.

Before Leo won the Oscar, Titanic was the highlight of his long, varied career. That may not be how DiCaprio sees it, 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 girl's bedrooms from Toronto to Tokyo. Our Prince of the City become King of the World. —Nathan Reese

Turns: 42

Big Moment: HE WON A FUCKING OSCAR!!!!!!!!!!!!

In 2016, Leonardo DiCaprio jumped from gorgeous model to gorgeous model—Ela Kawalec to Roxy Horner to Nina Agdal—and released a documentary about his main interest, climate change. But none of that matters. The world's supply of vaporizers could have run dry and 2016 still would be the best year of his life. Because 2016 is the year he won an Oscar (for The Revenant). 2016 is the year his life's work was validated. 2016 was the year he stopped *screaming internally*. Watch this video of Leo having his name inscribed on his Oscar and try to tell me that wasn't the high point of his life. —Andrew Gruttadaro