DiCaprio had a re-occurring role on ABC's Growing Pains and played Tobias Wolff in This Boy's Life, the latter which drew him high praise from critics. DiCaprio's momentum continued with What's Eating Gilbert Grape, where he played the mentally retarded brother of Johnny Depp. That role got him an Academy Award nomination. DiCaprio's momentum didn't continue though as he bombed in the movies The Quick and the Dead, The Basketball Diaries, and in Total Eclipse, where he played the homosexual poet Rimbaud. Leonardo atoned himself with spirited performances in Marvin's Room and Romeo + Juliet, but DiCaprio's ship literally came in when he played Jack Dawson in the big budget Titanic, which was the highest grossing film ever made. He then followed up with The Man in the Iron Mask, where he played a dual role as good and evil twin heirs to the French monarchy. His latest film, The Beach, netted DiCaprio a whopping $20 million in which he plays an traveler who is given a map to paradise by an unknown stranger. DiCaprio also is rumored to be eyeing the biographic film about Howard Hughes, the eccentric bisexual deceased billionaire.

Leonardo is perhaps the busiest actor in Hollywood at getting busy. He is in effect the Wilt Chamberlain of the stars. Although some have said he is a dud in bed, such as Linnea Dietrichson, a steamy Danish barmaid who says she got it on with Leo after meeting in a London pub. Unfortunately for her, she came away disappointed, saying he was spouting cliché pick up lines and lifeless kisses. She also said the moment of passion with what she termed as the flabby and pale DiCaprio only lasted 5 minutes. There also are reports that Leo is not endowed anywhere near that of John Holmes, as porn star Kendra Jade termed him 'average'. Perhaps was the impetus for him suing Playgirl magazine stopping them from publishing full frontal nudity of the actor in 1998. This might be refuted considering his reported naked romp in Cuba with supermodel Naomi Campbell, a rumored brat in her own right. Incidentally, DiCaprio met another model Carla Paneka while in Havana and was said to be getting dual action. He's been linked to many other's as well, including Kristin Zang (who reportedly dumped DiCaprio and broke his heart to the point where he stopped his Romeo ways for over a year), Vanessa Hayden, Kate Moss, Alicia Silverstone, Eva Herzigova (whom he literally stole from washed up Bon Jovi drummer Tico Torres to whom she was married!), his Juliet co-star Claire Danes, singing lolita Mariah Carey, French actress Virginie Ledoyen (who also co-stars in The Beach), the then married Demi Moore (which may have hastened her later divorce from Bruce Willis), Natasha  Henstridge, Carmen Electra, Helena Christensen, Juliette Lewis, Bijou Philips, Baby Spice, and his Titanic co-star Kate Winslett! There are many other lesser known names, and Leo and his 'gang' are always out on the town wherever they might be. What does Leo say about all this screwing around getting nude with supermodels and the like? "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."

There also are several reports of Leonardo being what some would call a punk. During Jennifer Lopez's 29th birthday party in New York, DiCaprio was partying with guy pal and rapper Q-Tip, until one of his ex-friends David Blaine showed up, when DiCaprio reportedly shouted "we're out of here!" and headed to the exits with his buddies. When leaving the club, Leo reportedly threw a beer bottle at the press barely missing a photographer, although others at the scene say it was no beer bottle. There was talk that Q-Tip is homosexual and Leo's past work and agressive sexual tendencies may indicate that perhaps reports of Leo being bisexual have some merit. Another report says that Leo was being an immaturish child who was flicking lights on and off at a party for Mary Fanaro in Malibu trying to get people to leave. When a woman tried to stop him, he allegedly slapped her hand and continued until Kate Hudson, daughter of Goldie Hawn, arrived. One of the partiers goes on to say in New York Magazine "He was like a spoiled kid who finally shuts up when you give him a new toy. All of a sudden, he was all over her."

Star Wars fans struck back at Leo when during a filming of The Phatom Menace, a trailer for The Beach caused the packed house to begin chanting "Leo sucks!" and it was originally reported that he was in the theater, but later reports deny that claim. Apparently Leo has thought Menace itself sucked, and he was rumored to have turned down the role as Anakin Skywalker in Episode 2 (in fact, Access Hollywood confirmed he turned down the role because of scheduling conflicts). His run-ins with James Cameron during the filming of Titanic and his questioning of the director made him even wonder why DiCaprio took the role in the first place. This all being said, DiCaprio has been seemingly an unfair target of the paparazzi as they continue to hound him to the where in Taiwan where security representatives reportedly blocked DiCaprio and crew's leaving until one of his friends apologized for cussing out a photographer. DiCaprio claims it was because the photographer was shouting obscenities about the man's parents.