The following year, Stiller debuted as a feature film director with the twentysomething angst romcom Reality Bites (1994), in which he also starred alongside Winona Ryder and a memorably grungy Ethan Hawke. The film was a relative critical and commercial success and scored with Gen-Xers; unfortunately, Stiller's next directorial effort, 1996's The Cable Guy, flopped. A black comedy that cast Jim Carrey as the psychotic title character, who perpetually molests client Matthew Broderick and refuses to leave his side, the film failed to register with critics and audiences, largely because of its uncertain approach to the material. After a small part as nursing-home orderly Hal in the Adam Sandler comedy Happy Gilmore (1996), Stiller rebounded with a starring role in David O. Russell's Flirting With Disaster (1996). The relatively positive reception afforded to that comedy helped to balance out the relative failure of Stiller's other film that year, If Lucy Fell. It was not until two years later, however, that Stiller truly stepped into the limelight. Thanks to starring roles in three wildly, wickedly different films, he emerged as an actor of versatility, equally adept at playing sensitive nice guys and malevolent hellraisers.

In the smash gross-out comedy There's Something About Mary (1998), Stiller appeared as the former type, making comic history for outrageous sight gags that involved misplaced bodily fluids and mangled genitalia. That same summer, Stiller did time as a gleefully adulterous theatrical instructor (with an irritating habit of gabbing during sex) in Neil LaBute's jet-black evisceration of contemporary sexual mores, Your Friends and Neighbors. Finally, Stiller starred in the intensely graphic and disturbing addiction drama Permanent Midnight, earning critical acclaim for his portrayal of writer-cum-heroin addict Jerry Stahl -- a personal friend of the Stiller family from Stahl's days scripting the TV series ALF. Now fully capable of holding his own in Hollywood, with the license to prove it, Stiller starred alongside William H. Macy, Paul Reubens, Hank Azaria, and pal Janeane Garofalo in the buttered popcorn blockbuster Mystery Men (1999) as the leader of a group of unconventional superheroes. Stiller also landed a supporting role in The Suburbans, a comedy about the former members of a defunct new wave band. The following year, Stiller starred as a rabbi smitten with the same woman as his best friend, a Catholic priest (Edward Norton), in the well-received romantic comedy Keeping the Faith (2000), which Norton also co-produced and directed. Stiller found his widest audience up to that point, however, with the Jay Roach-directed madcap comedy Meet the Parents.

As the tale of a nutty father-in-law to be (Robert De Niro) who wreaks unchecked havoc on his daughter's intended (Stiller) via covert CIA operations and incessant interrogation, this disastrously humorous tale of electrical interference gone wild scored with ticket-buyers and qualified as the top box-office draw during the holiday season of 2000. In the autumn of 2001, Stiller brought one of his most popular MTV Video Music Awards incarnations to the big screen in the outrageously silly male-model comedy Zoolander, in which he successfully teamed with (real-life friend) Owen Wilson to carry stupidity to new heights. In 2001 Stiller once again teamed with Wes Anderson collaborator Wilson for the widely praised comedy drama The Royal Tenenbaums. Cast as the estranged son of eccentric parents who returns home, Stiller infused his unmistakable comic touch with an affecting sense of drama that found him holding his ground opposite such dramatic heavies as Gene Hackman and Anjelica Huston.

Though his work in 2002 offered little more than a few cameo performances and some vocal contributions to various animated children's shows, the busy comedic actor returned to the big screen for the 2003 comedy Duplex, directed by Danny DeVito. Though the film pairs Stiller and Hollywood bombshell Drew Barrymore as a couple willing to go to horrific extremes to land the much-desired eponymous living space, reviews were unkind and the comedy died a quick death at the box office. Stiller's next film -- the romantic comedy Along Came Polly -- fared considerably better on a fiscal level, but suffers from one unshakable problem: the complete implausibility of the central premise. Moreover, to many, it seemed almost desperate, at times, to top There's Something About Mary from the twin standpoints of scatology and raunch.

Spring 2004 promised a rebound when the electrifying duo of Stiller and Owen Wilson returned to the big screen with director Todd Phillips' celluloid recycling job Starsky & Hutch. Though Stiller and Wilson seemed the ideal pair for such a conceptually rich re-imagining of 1970s television, and the film boasted wonderful villainous turns by rapper Snoop Dogg and Vince Vaughn, reviews were once again lackluster and the film struggled to find an audience. Yet Starsky & Hutch did actually reap a profit, which (in a business sense) placed it miles ahead of Stiller's next film. Released a mere two months after Starsky & Hutch, the Barry Levinson comedy Envy sports a wacky premise; it explores the comic rivalry that erupts between two longtime friends and neighbors when one invents a product that makes dog excrement disappear.

It also boasts a marvelous cast, replete with Stiller, the maniacal Jack Black, and the brilliant Christopher Walken. But for whatever reason (speculated by some as the film's inability to exploit the invention at the story's center) the film's sense of humor failed to catch fire and Envy died a quick box-office death. Stiller fared better with the ribald, anarchic summer 2004 comedy Dodgeball: A True Underdog Story, starring himself, Vince Vaughn, and Rip Torn. For the following two years, Stiller once again contented himself largely with bit parts (2004's Anchorman: the Legend of Ron Burgundy, 2006's Tenacious D in the Pick of Destiny) until the Christmas 2006 release A Night at the Museum.

In this effects-heavy fantasy, adapted from the popular children's book by Milan Trenc, Stiller plays Larry Daley, the new night watchman at New York City's Museum of Natural History, who discovers that the exhibits all spring to life after hours, from a giant skeletal Tyrannosaurus Rex to a waxen Teddy Roosevelt -- and seem content to hold Larry hostage. With supporting turns from such old pros as Dick Van Dyke and Mickey Rooney (reunited onscreen for one of the first occasions since 1969's The Comic) and magnificent special effects, the effort split critical opinion, but shot up to become one of the top three box-office draws during the holiday season of 2006. Meanwhile, Stiller signed on to team with the Farrelly brothers for The Heartbreak Kid (2007), a remake of the 1972 Elaine May comedy of the same title; he also produced Blades of Glory, a comedy with Will Ferrell and Jon Heder as rival figure-skating champions vying with one another for Olympic gold.