After knocking around NYC for a while struggling to break into show business, Kaufman finally caught a break in 1991 when he was hired as a staff writer on the quirky Chris Elliott sitcom "Get a Life!" (Fox, 1990-92). The two episodes he penned, about a female ex-con who takes Elliot prisoner and about Elliot drinking a concoction that allowed him to travel back in time both displayed elements of the surreal which would come to be a Kaufman hallmark. He went on to write some 30 episodes of TV shows ranging from the ensemble sketch comedy "The Edge" (Fox, 1992-93) to more conventional sitcoms like Fox's "Ned and Stacey" during its second season (1996-97).

While earning a living working in television, Kaufman was nurturing his dream project. Begun as "a story about a man who falls in love with someone who is not his wife" the script eventually evolved to include elements of whimsy and inventiveness. He included such oddball details as having his hero be a puppeteer who eventually finds work on the 7 1/2 floor of a Manhattan office building, a randy centenarian boss and eventually the actor John Malkovich. Reportedly Kaufman selected the latter for several reasons, including the fact he is a gifted actor as well as for the lilt of his name which when repeated frequently can seem hilarious. Convincing the actor to give his permission to use his name and to play this version of himself took some doing, but once he agreed, the project moved forward. The cast, including Catherine Keener, John Cusack and Cameron Diaz, all signed on because of the originality of the material. As Diaz described it, "they say in Hollywood there are only 14 scripts. Well this is number 15." From its initial screenings, "Being John Malkovich" generated positive buzz and its inclusion at various film festivals before its theatrical release led to its cachet. Kaufman and its director Spike Jonze were set to reteam, with Jonze as producer on "Human Nature" (2001), another surreal relationship story about a hirsute woman who falls for a man with a tiny penis.

On the big screen, Kaufman continued to cultivate a close relationship with director Jonze, producing his script "Human Nature" in 2001. In 2002 the pair reteamed for the remarkable reality-bending film "Adaptation," which featured Kaufman himself (portrayed by Nicolas Cage) as the central character, a timid, flabby, balding, sweaty, anxiety-ridden screenwriter struggling a to adapt author Susan Orlean's best-selling novel "The Orchid Thief" into a motion picture script. Inspired, existential, loopily funny, poignant and unabashedly eccentric, "Adaptation" was a work of extreme originality, flip-flopping between fact, fiction and fantasy while depicting both the apparently self-loathing Kaufman's angst-ridden life and major plot elements from the book by Orleans (played by Meryl Streep), which chronicled her encounters with real-life Miami orchid thief John Laroche (Chris Cooper). Kaufman employs a fictional twin brother, Donald (also Cage), as his own opposite number, a carefree, script-structure-savvy aspiring writer who, unlike Charlie, slavishly and successfully figures out the formula for cranking out typical Hollywood fare-ironically Donald is the vehicle for teaching the on-screen Charlie the kind of epiphany-style life lessons Kaufman vehemently resists in his own work. While the Donald character serves as an alter ego for Charlie, he is never directly revealed to be an imaginary creation in the film -- Indeed, "Donald Kaufman" receives co-screenplay credit and Charlie dedicated the script in Donald's memory. Also in 2002, George Clooney made his directorial debut with the Kaufman-penned "Confessions of a Dangerous Mind," a adaptation of the presumably fictionalized and farcical autobiography of game show producer and host Chuck Barris ("The Gong Show"), who claimed to lead a double life as a CIA assassin.

As Kaufman's cachet grew among Hollywood actors looking to take on unconventional projects, he delivered his most accessible and surprisingly romantic work to date, "Eternal Sunshine of the Spotless Mind" (2004), for which he wrote the screenplay after collaborating on the story with Pierre Bismuth and the film's director, Michel Gondry (who helmed "Human Nature"). The movie cast Jim Carrey and Kate Winslet as a pair of lovers who traumatic breakup leads them to a company that can erase painful memories--the film attracted an steller supporting cast including Elijah Wood, Kirstin Dunst, Mark Ruffalo and Tom Wilkinson, and earned critical raves. Although released much earlier than the usual "awards season" fare, the film made such a strong impression that it ultimately collected numerous awards and nominations and, most notably, took home honors for Best Original Screenplay at the BAFTA Awards, the Writers Guild of America Awards and, ultimately, the Academy Awards.