DiCaprio was next cast alongside Johnny Depp in "What's Eating Gilbert Grape?" (1993), Lasse Halstrom's evocative version of Peter Hedges' coming-of-age novel. The good looks of the green-eyed blond nearly lost him the part of the sloppy-looking Arnie, Gilbert's mentally challenged but cheerful younger brother. The 19-year-old actor again snared the best reviews as well as a Best Supporting Actor Oscar nomination for his performance.

DiCaprio lost out to Christian Slater in his effort to land the small but essential role of the "boy" reporter in "Interview With the Vampire" (1994). He tried his hand at another exceedingly stylish genre film with a supporting role opposite Sharon Stone in Sam Raimi's delirious meta-Western "The Quick and the Dead" (1995). DiCaprio brought verve and cynicism to his portrayal of the Kid, a cocksure young gunslinger who may be the son of baddie Gene Hackman. He veered back to the margins to star in the long-awaited (and profoundly disappointing) adaptation of "The Basketball Diaries" (also 1995), Jim Carroll's gritty memoirs of a youth that incorporated good grades, local basketball stardom and heroin addiction. DiCaprio won praise for his highly emotional performance but the film was deemed aimless, shallow and routine.

Courting the art-house crowd, DiCaprio portrayed the young French poet and arrogant, self-styled "genius" Arthur Rimbaud in Agnieszka Holland's problematic film version of Christopher Hampton's play "Total Eclipse" (1995). This psychological drama traced the complex and exceedingly unpleasant sexual relationship between the youthful Rimbaud and his older mentor, Paul Verlaine (David Thewlis), while failing to deal with their art. A critical and commercial flop, the film marked DiCaprio's first unqualified disaster since achieving celebrity. He seemed poised to bounce back as half of everybody's favorite pair of doomed lovebirds in the eagerly awaited "William Shakespeare's Romeo and Juliet" (1996). Paired with rising star Claire Danes, DiCaprio strove to create a "more hard-core" Romeo for this bizarrely stylized and anachronistic take on the classic helmed by Australian director Baz Luhrmann ("Strictly Ballroom"). Later that year, he was featured as Meryl Streep's troubled teenaged son in "Marvin's Room.”

DiCaprio next landed the lead role in director James Cameron's lavish spectacle "Titanic," playing Jack Dawson, a plucky, impoverished American artist who wins a third-class ticket on the historically doomed luxury liner and enters into a star-crossed love affair with a young Philadelphia socialite (Kate Winslet). The film went on to become both a blockbuster and a bona fide phenomenon, becoming the all-time highest grossing film in history. Although some bemoaned the fact the he did not receive an Oscar nomination, DiCaprio clearly reigned supreme as the hottest male box office attraction of the moment; indeed, much of the repeat business was credited to a legion of young female fans who became enthralled with the actor. After the one-two punch of "Romeo" and "Titanic," his heartthrob status was secured and, despite reigning back on the amount of screen roles he accepted, he became an object of media fascination for several years to come.

DiCaprio continued in period fare with the dual role of French King Louis XIV and his doppelganger in the 1998 remake of “The Man in the Iron Mask," delivering another dashing performance but failing to ignite "Titanic"-sized box office return. In 2000 he teamed with hard-edged director Danny Boyle for "The Beach" (touted as a "comeback" vehicle for the actor), an uneven vehicle in which he plays an American searching for lost treasure on a secluded Asian island. DiCaprio's performance was better than the story deserved, and again it failed to spark with all but his most die-hard fans. Things were looking up in 2001 when the actor was cast in director Martin Scorsese's 19th Century drama "Gangs of New York," playing Irish-American immigrant Amsterdam Vallon, released from prison and intent on taking on the gangs that killed his father. Production issues and reported squabbles between Scorsese and the studio delayed the film by nearly a year to the 2002 holiday season. DiCaprio found himself going up against...himself in director Steven Spielberg's "Catch Me If You Can," in which he played real-life con artist Frank W. Abagnale, who successfully pulled off dozens of scams in various identities and became the youngest man on the FBI's most wanted list. Perfectly cast, DiCaprio delivered his most charming and mature performance to date, proving himself again as both movie star and actor.

DiCaprio reunited with Scorsese on "The Aviator" (2004), a project the actor initially planned to do with director Michael Mann focusing on the prime years of the famed billionaire Howard Hughes. Although many felt DiCaprio's boyish looks were not ideally suited for the role, the actor delivered one of his strongest performances yet, convincingly portraying Hughes' multifaceted qualities: as a young mogul-in-the-making taking Hollywood by storm; as one of Tinseltown's most notorious ladies' men; as a pioneer of aviation and an enterprising maverick who took on the U.S. government; and most compellingly as man whose potential is crippled by obsessive-compulsive disorder. As the centerpiece of Scorsese's strongest, boldest work in nearly a decade, DiCaprio again delivered on his own early promise, smoothly maturing into more adult and more challenging roles, and he was rewarded with a Golden Globe award for Best Performance by an Actor in a Motion Picture - Drama. His bravura performance also earned DiCaprio his second career Academy Award nomination—and first in the Best Actor category.

After the success of "The Aviator" the actor immediately reunited with Scorsese to join an all-star cast that including Matt Damon, Mark Wahlberg and Jack Nicholson for "The Departed" (2006), playing a Boston cop assigned to work undercover inside a notorious Irish-American gang who rises up the ranks to a senior level, even as a member of the gang infiltrates the police force—a story loosely based on the excellent Hong Kong action thriller “Infernal Affairs” (2002). As “The Departed” earned mostly good reviews prior to its early October debut, DiCaprio awaited the release of his next film, “Blood Diamond” (2006), a sweeping tale directed by Edward Zwick about a South African diamond smuggler (DiCaprio) and a poor fisherman (Djimon Hounsou) who join forces in order to find a rare pink diamond that can transform both their lives. DiCaprio earned Golden Globe Award nominations for Best Performance by an Actor in a Motion Picture for both “The Departed” and “Blood Diamond.” Also for the latter, he received an Academy Award nomination for Best Actor, surprising many that he did not get a nod for "The Departed." Then in a change of pace, DiCaprio signed on to narrate “11th Hour” (2006), a documentary that examined global warming and possible solutions to restore the planet’s decaying ecosystems.