In 1991, he saw "Slacker", Richard Linklater's comedy about shiftless youth. Inspired by both the feature and the possibility of low-budget moviemaking, Smith contacted former film school classmate Scott Mosier. In late 1992, Smith wrote the script for "Clerks", a somewhat plotless slice-of-life look at life from behind the counter at a convenience store. With Smith directing, Mosier producing and moneys raised from Smith's former college tuition fund, the sale of his extensive personal comic collection, plus loans from Mosier's parents and credit cards, the duo made "Clerks" in 21 nights, filming in the very Quick Stop in which Smith was working by day. A screening at the Independent Feature Film Market conjured a buzz for their efforts, and "Clerks" went on to become the toast of the Sundance Film Festival in January 1994, sharing the Filmmaker's Trophy with Rose Troche's "Go Fish".

The quirky "Clerks" earned Smith an agent at Hollywood's CAA powerhouse and a distribution deal with Harvey and Bob Weinstein of Miramax. More acclaim and awards followed at the Cannes Film Festival, but the MPAA ratings board determination that it should receive an 'NC-17' for language delayed the commercial release of the film. Enlisting Harvard law professor and noted attorney Allen Dershowitz in their cause, Smith and Mosier appealed the decision, and the film eventually got its 'R' rating and a release in late 1994. Playing in a limited number of theaters, many of them art-houses, "Clerks" grossed more than $1 million and garnered critical acclaim. By then, Smith was already at work on his next effort, "Mallrats" (1995), a look at youth at a mall over the course of a weekend. Funded by distributor Gramercy for $5.8 million, "Mallrats" earned lukewarm critical notices and an anemic box office.

Returning to his indie routes, Smith made the critically-acclaimed "Chasing Amy" for $250,000. The film, about the unlikely relationship between a bisexual woman and a comic book writer, grossed $12 million for Miramax and spelled redemption for the filmmaker. He and Mosier also urged the Weinsteins to buy the Ben Affleck-Matt Damon script for "Good Will Hunting" (both 1997) from Castle Rock for $800,000 and shared co-executive producing credit for what became Miramax's highest grossing picture (as of 1998). Smith merged his passions for film and comics when he wrote a screenplay for "Superman Lives" which Tim Burton was assigned to direct. Conflicts with Warner Bros. and Burton, however, relegated it to the trash heap. He departed from the boy-girl relationship format of his previous movies for "Dogma" (1999), a semi-controversial religious satire about two fallen angels trying to re-enter Heaven starred Linda Fiorentino, Damon and Affleck and featured George Carlin, Chris Rock, Salma Hayek and Bud Cort, among others. His next effort was a lighthearted romp starring his recurring side characters Jay & Silent Bob (played by Jason Mewes and Smith himself, the sidekicks had appeared in each of Smith's films in roles of varying importance) in the antic "Jay & Silent Bob Strike Back" (2001). In the film--which was visually junky but had several amusing sequences and classic Smith dialogue--the writer-director brought back many of the characters from his previous films (what he calls the View Askew universe, after his production company), including his close buddy Ben Affleck as both Holden from "Chasing Amy" and a parody version of his movie-star self.

The writer-director, always a dazzling racounteur and a canny self-promoter, also had forays into television, turning his "Clerks" into a short-lived animated series for ABC, which aired in 2000. Beginning in 2002 Smith joined NBC's "The Tonight Show With Jay Leno" on a recurring basis for short filmed comedy bits. Among the more amusing were the collection of Smith's snarky road trips across America visiting "Roadside Attractions" like giant balls of twine, and short films like "The Flying Car" featuring the "Clerks" characters yet again, trapped in traffic discussion what they would do to have a flying car like the Jetsons.

Smith also put his career as a writer of comics firmly on track with the debut of "Clerks (the Comic)" in 1998 (followed by comic book adventures of Jay & Silent Bob) and his collaborations on Marvel Comics' "Daredevil" and DC's "Green Arrow," though his track record faltered in 2002 when his movie career reheated and he failed to finish (as of 2004) his runs on the mini-series "Spider-Man: Black Cat" and "Daredevil: Bullseye"--something fans always enjoy skewering him about. Indeed, it was his collected paperback run of "Daredevil" that lured his friend Affleck, another childhood fan of the character, to pen a glowing introduction, which in turn inspired Marvel Productions and 20th Century Fox to lobby successfully to cast the actor as the blind superhero in the 2003 film. Smith also had a cameo role, playing a morgue attendent named Jack Kirby, after the prominent Marvel comic book artist. He also became one of the first filmmakers to engage in regualr, near-direct dialogue with his audience, communicating via the Internet through his web sites MoviePoopShoot.com and ViewAskew.com.

During the media furor surrounding the "Bennifer" romance between Affleck and Jennifer Lopez, Smith often found himself acting as an unofficial spokesperson for the couple, given his closeness to Affleck and the fact the couple were both appearing in his romantic comedy "Jersey Girl" (2004). When the pair's previous film outing "Gigli" (2003) was labled a bomb of epic proportions and the relationship subsequently fell apart, Smith and his film's marketers made a painstaking effort to point out that Lopez's role was pivitol but brief in an effort to distance his film from the "Gigli" catastrophe. Instead, "Jersey Girl" (which opened to mixed reviews and unspectacular box office but came nowhere near the flop that was "Gigli") focused on Affleck as a driven, urban p.r. exec who becomes a widowed single dad stuck in the Jersey suburbs with his dad and his daughter, and unexpectedly gets a second chance at love. Smith threw out much of his juvenile humor (it would be his first film without Jay & Silent Bob, for example) and attempted to tell a more straightforward, romantic story, with mixed success.