Crystal made his film debut during a hiatus from "Soap", playing the world's first pregnant man in the little-seen "Rabbit Test" (1978), directed by Joan Rivers. He later performed the small role of Morty the Mime in Rob Reiner's "This Is Spinal Tap" (1984). Crystal's feature career resumed with "Running Scared" (1986), a ho-hum police action comedy pairing him with Gregory Hines. Crystal emerged with positive notices and went on to a delightful bit in Reiner's romantic fantasy "The Princess Bride" (1987). He consolidated his box-office standing as the romantic lead of Reiner's hugely successful "When Harry Met Sally" (1989) opposite Meg Ryan and as a listless radio exec who overcomes a mid-life crisis by going on a Western-style cattle drive vacation in "City Slickers" (1991). The latter marked Crystal's first collaboration with the crackerjack comedy writing team of Lowell Ganz and Babaloo Mandel.
Crystal provided the story and served as executive producer for "City Slickers" but desired even greater control on his next project. In addition to producing, co-writing (with exec producers Ganz and Mandel) and starring, Crystal took up the directorial reins with "Mr. Saturday Night" (1992). This boldly schmaltzy and sometimes hilarious film chronicled 50 years in the life of veteran comic Buddy Young Jr., a fictional character he had played on "SNL" and other shows since originating him on a 1984 HBO special. Crystal has long evinced a love of both affectionately broad ethnic characterizations and equally broad "Vegas-style" entertainers. Associates have remarked that he eagerly looks forward to becoming an old Jewish comic. Clearly "Mr. Saturday Night" was a deeply heartfelt project but reviews were mixed and audiences stayed away. He fared better at the boxoffice after getting back in the saddle to produce, co-script, and star in the pleasant if unremarkable sequel "City Slickers II: The Legend of Curly's Gold" (1994). But his next effort, the romantic comedy "Forget Paris" (1995) with Debra Winger failed to excite critics or audiences.
Despite all his other successes, Crystal may be best known and loved for his frequent duties as a TV host. Crystal has been an exuberant host for more than 20 special events since 1979--including the Grammy Awards in 1987 and 1988--and has won several performing and writing Emmys for his efforts. He became known as one of the best hosts of the annual Oscar telecast beginning with his first ceremony in 1990--Crystal won audiences with inventive routines that found him plugged into film clips or singing hilarious songs about the current crop of nominees. He returned again in 1991 and had a standout performance at the 1992 Oscar telecast, getting much improvised mileage from his "City Slickers" co-star Jack Palance's impulsive decision to begin performing one-handed pushups on stage after accepting his Oscar. Along with his colleagues Robin Williams and Whoopi Goldberg, he has been co-hosting the popular "Comic Relief" benefit specials on HBO since 1986.
In 1997, Crystal and Williams teamed onscreen for the pallid comedy "Father's Day", which proved to be a box-office disappointment. After returning as host of both the 1997 and 1998 telecasts of the Academy Awards, he attempted another screen comedy as writer, producer and star of "My Giant" (1998), portraying a cynical Hollywood agent who represents a very tall, gentle Romanian (played by Washington Bullets basketball player Gheorghe Muresan). Crystal had a career resurgence in 1999 when he appeared as Ben Sobol, a nervous psychiatrist beset with a vicious Mafia boss (Robert DeNiro) as his needy patient in director Harold Ramis' "Analyze This." The actor reprised the role for the less-fresh sequel "Amalyze That" (2002). Proving that he could still be more than a stellar Academy Awards host (a role he reprised in 2000), Crystal took a hiatus from his famed emcee duties, but the on-screen results of his new career focus were mixed: he earned an Emmy nomination for directing the HBO telepic "61*" which focused on the hitting race between Mickey Mantle and Roger Maris, and he scored kudos for his voice duties as Mike Wazowski in Disney/Pixar's animated hit "Monsters, Inc." (2001) but his next film as an actor and co-writer, "America's Sweethearts" (2001), in which he co-starred with Julia Roberts, Catherine Zeta-Jones and John Cusack, was a startlingly unfunny attempt to lampoon Hollywood--although to his credit Crystal provided the only genuinely amusing moments in the movie.
Crystal reassumed the Oscar hosting duties for the 2004 Academy Awards, his eighth outing as master of ceremonies. Other than his Oscar and other hosting gigs, Crystal had not appeared on the live stage in over 15 years when he decided to launch his next project on the Broadway stage in 2004. His autobiographical one-man show "700 Sundays"--derived from the amount of days the comic spent with his jazz manager father before he died when Crystal was just 15--featured Crystal in a variety of roles as he revisited his formative years. The show played to capacity crowds at New York's Broadhurst Theater throughout its run, and was extended beyond its initial booking, earning a Tony for Best Theatrical Event. That same year he released a top-selling children's story inspired by the birth of his granddaughter titled I Already Know I Love You.