Drawn particularly, if not exclusively, to comedy in his assignments as a cinematographer, Sonnenfeld performed lensing chores on Danny DeVito's "Throw Momma from the Train" (1987), Rob Reiner's "When Harry Met Sally . . ." and Penny Marshall's "Big" (both 1988) before earning his first feature credit as a second unit director while shooting Reiner's wintry "Misery" (1990). Sonnenfeld then segued to the director's chair with "The Addams Family" (1991), an ornately stylish film adaptation of Charles Addams' cartoons (also inspiration for the classic 60s sitcom), which, despite repetitious humor and a throwaway plot, earned over $110 million at the box-office. He followed-up by directing a typical Michael J Fox romantic comedy vehicle, "For Love or Money" (1993), which garnered little attention from press or public, before helming a superior sequel (though not a bigger money-maker), "Addams Family Values" (1993). Bolstered by sharp ensemble playing (with young Christina Ricci a standout), this effort was more consistent, thanks to somewhat more coherent screenplay from playwright-turned-screenwriter Paul Rudnick.

Sonnenfeld had played a key role in developing "Forrest Gump" (1994), suggesting that the fat, strong Gump of Winston Groom's novel be a lanky, fast guy on-screen; commissioning Eric Roth's script; and bringing Tom Hanks, a friend since "Big", on board before deciding to make "Addams Family Values" instead. Though he regretted his choice for some time, his career didn't suffer as he immediately enjoyed his first critical hit with "Get Shorty" (1995), a humorous, literate and well-nuanced Elmore Leonard adaptation boasting a dream cast including John Travolta, Danny DeVito, Gene Hackman and Rene Russo. Here the director proved he could make a mainstream movie that relied more on acting and dialogue than gimmickry without compromising his love of blacker-than-black humor. Sonnenfeld executive produced, as well as portrayed a doorman, losing out in his battle with his editor who insisted that the doorman footage not be cut. He also managed to helm some commercials, including the first batch of Duracell ads featuring the mean-spirited, battery-powered Puttermans. Duracell defanged the Puttermans for subsequent ads, prompting Sonnenfeld to say: "I was saddened to see how quickly they gave up on being a little darker. They chickened out."

Sonnenfeld delivered the biggest blockbuster of 1997, the ultra-hip sci-fi comedy "Men in Black", accomplishing what Tim Burton had failed to do with the campy "Mars Attacks!" (1996)--a close encounter of the truly funny kind. Immediately after coming on board, the director had requested a rewrite, setting most of the action in New York City and patterning it not after classic sci-fi but on "The French Connection" (1971). Instead of Gene Hackman as Popeye Doyle with a guy up against the bathroom wall, he gave the audience Tommy Lee Jones interrogating an alien "stoolie" in the guise of a dog. Drawing from the popular urban legend that aliens are here among us, Sonnenfeld teamed with multiple Oscar-winner Rick Baker to design the alien puppetry, but the best gag of all was the screen that kept tabs on registered aliens who qualify as celebrities, showing the likes of infomercial guru Tony Robbins, Newt Gingrich, Sylvester Stallone, psychic friend Dionne Warwick, ILM chief George Lucas and Steven Spielberg (who would allow it only if Lucas said OK too). Sadly, Sonnenfeld couldn't get permission from everyone on his alien wish list. "I wanted Michael Jackson very badly. He wouldn't do it . . . None of the real aliens would."

Back in Elmore Leonard country, Sonnenfeld executive produced Steven Soderbergh's underrated "Out of Sight" (1998) and executive produced (the series) and directed the highest-rated network pilot premiering in the summer in four years, ABC's "Maximum Bob,” which he had originally considered doing as a feature before opting for the expanded format seven episodes afforded. He also executive produced ABC's ill-fated remake of "Fantasy Island" (1998-99), inserting Malcolm McDowell into the role of Rourke to take advantage of the actor's dangerous, edgy charm and make the character more controlling ("like the devil") than depicted originally by Ricardo Montelban. "Television all looks the same ... I want to take something that is banal and put my own absurdist twist on it." Also one of the executive producers for UPN's "Secret Agent Man" (2000), Sonnenfeld had by no means renounced the large screen in favor of the small screen—his next feature was a remake of a classic 60s Western series, "Wild Wild West" (1999). Reuniting with Smith as an 1800s James Bond, Sonnenfeld announced, "We will absolutely address the fact that this time, our lead character is a black man during this period in time. It's a concept we're embracing a lot." Professing that the movie would be bigger than "Men in Black" ("We've got an 80-foot tarantula in this movie"), he hoped audiences would agree and deem it the "cool" movie of the summer. It wasn't.

Sonnenfeld’s next feature, the inevitable sequel “Men in Black II” (2002), proved to be almost as successful as the original, but not nearly as well-received by critics. Because of the success of the first movie—it grossed almost $600 million worldwide—Sonnenfeld felt the pressure of having to execute. Adding grist to the mill was a looming actor’s strike, an unfinished script and unwanted meddling from producers. Two weeks into shooting, Sonnenfeld spent a night at New York University hospital thinking he was suffering a heart attack. It was only anxiety. But he used the emergency to his advantage—the producers were nicer to him and he managed to get the script changes he wanted. Sonnenfeld eventually managed to get the movie made, getting it ready for release on the 4th of July where it took in over $52 million opening weekend and $450 million worldwide. His next project, “Big Trouble” (2002), adapted from humorist Dave Barry’s debut crime novel, more than lived up to its unfortunate title. Originally set for release in late September 2001, the film was pushed back because of its proximity to the terrorist attacks on September 11th—not to mention a subplot involving a bomb on an airplane. “Big Trouble” was rescheduled for release in April 2002, as a confident Sonnenfeld predicted audiences would find his movie hysterical. Turned out audiences steered clear of “Big Trouble” at the multiplexes—the $40 million movie made a painful $7 million in total box office receipts.

Sonnenfeld stepped back from his directing duties to focus on producing. In 2004, he was an executive producer on “Lemony Snicket’s a Series of Unfortunate Events,” starring Jim Carrey as the frightful Count Olaf whose dastardly designs on the family fortune of three orphans leads to plots of even more dastardly designs. Sonnenfeld also served as a producer on “The Ladykillers” (2004), a remake of the 1955 Alec Guinness-Peter Sellers black comedy. The film was made by old friends Joel and Ethan Coen, but the team’s previous magic failed to resurface. Meanwhile, Sonnenfeld returned to the director’s chair with “RV” (2006), a rather one-note comedy starring Robin Williams as an over-worked executive (Robin Williams) who drags his family on a road trip from hell to Colorado in an RV he barely knows how to drive. Along the way, they encounter a clan of fanatical RV enthusiasts, forcing them to band together and become a family again—if they can avoid driving each other insane. Despite poor reviews, “RV” took its opening weekend with a $16 million haul at the box office.