A self-described "slob" who has been named repeatedly to People magazine's Worst Dressed List, Manhattan began fashioning his career as a Gen-X Renaissance Man, publishing a modestly-acclaimed novel, co-founding a Manhattan theater company, and stepping behind the camera to helm music videos and films, in addition to acting. Possessing Waspish good looks and a disarming air of sincerity, he began taking acting classes at Princeton University's McCarter Theater, and his stage debut there at age 13 in "St. Joan" led to a successful audition for "Explorers" (1985), Joe Dante's underappreciated teen sci-fi film (which also marked the feature debut of River Phoenix). The film flopped, and Hawke, encouraged by his mother, left acting for several years before returning with a well-received performance as a shy, sensitive prep school student in Peter Weir's "Dead Poets Society" (1989), followed quickly that same year by "Dad", in which he played Jack Lemmon's grandson.

Hawke's early films invariably cast him in coming-of-age roles, and though he gave a strong performance as a young prospector in the Disney version of Jack London's adventure "White Fang", he also took the black comedy "Mystery Date" (both 1991), despite realizing the script had problems. He made his Off-Broadway debut in the New York Shakespeare Festival production of "Casanova" that year before returning to student mode for "Waterland" (1992), an arresting British film about a desperate, middle-aged high school history teacher (Jeremy Irons seemingly trapped by his past. Hawke was also forceful and credible as the narrator and reluctant squad leader in the underrated but eloquent, antiwar drama "A Midnight Clear" (also 1992), adapted from the WWII-era novel by William Wharton. During a busy 1993, he appeared in three features (most notably "Alive", a surprisingly upbeat story about survival after a plane crash in the Andes); wrote, directed and edited the short film "Straight to One" about a pair of young honeymooners; and co-founded Malaparte., a not-for-profit theater group in NYC.

Hawke enjoyed a high profile lead as Winona Ryder's grubby, cynical boyfriend with artistic pretensions in the Gen-X romantic comedy "Reality Bites" (1994), which opened to extremely mixed reviews and disappointing box office. He went on to team with Richard Linklater for the first time on "Before Sunrise" (1995), a radical departure from the Texas slacker scene of the director's first two features. A European train journey introduces Hawke to the beautiful Julie Delpy and their mutual attraction causes them to detrain and explore Venice, sharing their first kiss on the same Ferris wheel Orson Welles featured in "The Third Man" (1940). Linklater's literate, sensitive treatment of a brief romantic interlude between two young people with their lives stretching out before them upped Hawke's sensitive hunk quotient with the ladies, who were certain he was just the man to listen attentively to their hopes and aspirations. He then disappeared from the screen for two years to write a novel, "The Hottest State" (Little, Brown, 1996), which garnered him ridicule, despite some good reviews and one critic telling him, "Well, I was going to put it on my list of the year's 10 best books. But then I figured you didn't need it." (Daily Telegraph, February 11, 2000).

After undergoing an intense exercise regimen with a personal trainer, Hawke returned to the screen looking buff for his first "adult" role in the futuristic thriller "Gattaca" (1997), his biggest-budget feature to that time. He delivered a strong performance as a genetically-inferior man who assumes the identity of a superior athlete in order to realize his dream of space travel. He also got the girl on screen and off, later marrying co-star Uma Thurman Alfonso Cuaron's modern-day version of "Great Expectations" (also 1997) teamed him romantically with Gwyneth Paltrowand gave him a chance to act with Robert De Niro, though the box office numbers were uninspiring. He then reteamed with Linklater alongside Matthew McConaughey, Skeet Ulrich and Vincent D'Onofrio for the Texas director's biopic of the bank-robbing "The Newton Boys" (1998), playing Jess Newton, the drunken, charming brother. He also had small roles in "The Velocity of Gary", which reunited him with executive producer-star D'Onofrio, and in "Joe the King" (both 1999), the feature directorial debut of his Malaparte. mate Frank Whaley.

Hawke once again provided a film's still center as star of Scott Hicks' "Snow Falling on Cedars" (1999), essaying an American journalist in a doomed interracial love affair. Having never remained long from the stage, he appeared as Kilroy in that year's Williamstown Theatre Festival revival of Tennessee Williams' "Camino Real" before taking on the Bard as Michael Almereyda's Gen-X "Hamlet" (2000), delivering the immortal "To be or not to be" monologue in the aisles of a Blockbuster video store. The youngest actor to ever play the role onscreen, Hawke's "slacker prince" came across a bit too bland, allowing supporting players Sam Shepard (as the ghost of Hamlet's father) and Kyle MacLachlan (as the usurping Claudius) to steal this engaging "Hamlet"-lite. He reteamed with Julie Delpyfor one scene in Richard Linklater's eye-popping animated feature "Waking Life" and then starred with his wife, Uma Thurman and Robert Sean Leonardin Linklater's digitally-shot "Tape" (both 2001). That same year, Hawke held his own opposite Denzel Washington playing a rookie L.A. policeman paired with a loose cannon partner who plays by his own rules in the uneven "Training Day". While Washington earned the lion's share of critical acclaim, Academy voters didn't overlook the younger actor's contributions and bestowed on Hawke a Best Supporting Actor Oscar nomination.

Having directed a short and a music video, it was only to be a matter of time before Hawke would turn his attention to feature filmmaking. Joining the ranks of those intrigued by digital video, he shot "Chelsea Walls" (filmed in 1999; released theatrically in 2002), an adaptation of Dylan Thomas' "Under Milkwood" set at NYC's famed Chelsea Hotel. Among the ensemble cast were Thurman and old Malaparte. pals Frank Whaley, Steve Zahn and Robert Sean Leonard Hawke also had a featured role in Whaley's second film "The Jimmy Show" (2002) and found time to write and publish a second novel, "Ash Wednesday" (Alfred A. Knopf, 2002).