Lost Roles is a weekly column that takes a particular comedic performer or writer and dives deep into all of their movie and TV projects that came close to happening but didn’t, for one reason or another. This week, we turn our attention to Dave Chappelle, who eight years ago was the hottest comedian in the country.

After spending more than a decade honing his chops as a stand-up comedian and appearing in supporting roles in other people’s movies (and a starring role in his own, Half Baked), Dave Chappelle finally found the perfect vehicle for comedy in the Comedy Central sketch show Chappelle’s Show in 2003.

Chappelle’s Show quickly became too popular for the star to handle, setting DVD sales records, scoring Emmy multiple nominations, giving life to irritating catchphrases that would frustrate Chappelle when fans yelled them at him during his stand-up sets and in his personal life, and netting Chappelle a whopping $50 million paycheck for the next two seasons. Dave Chappelle soon grew frustrated with the show’s raging popularity, his diminishing creative control, a hostile work environment, and was just generally feeling burnt out from two years of doing triple duty as a writer, actor, and producer on the show. So, Chappelle fled the country and hasn’t returned to TV or film since. He has, however, been performing stand-up regularly since the collapse of his Comedy Central series and recently joined Twitter, fueling speculation that he’s mounting a comeback, only to seemingly abandon his Twitter account after just a few days.

With this column, it’s often most fascinating to look at the abandoned projects and casting close calls of comedians who have retreated from the spotlight, and few in the comedy industry have ever walked away from a more flourishing career than Chappelle’s. With the overwhelming success of his Comedy Central series, particularly its second season in 2004, Dave Chappelle found himself receiving lucrative film offers, with competing TV networks salivating over him too. Let’s take a look at some of the projects Dave Chappelle came close to being involved in over the years but didn’t, including movies that would have seen him collaborating with Tom Hanks, Darren Aronofsky, and Michel Gondry, and biopics that would have seen him portraying street comic Charlie Barnett and funk icon Rick James, presumably without the worn-out catchphrase.

1. Forrest Gump (1994)

The role: Bubba Blue

Who got it: Mykelti Williamson

Early on in his career, Dave Chappelle turned down the role of Forrest Gump’s sidekick Bubba, according to IMDb, and regretted the choice later on when he saw how successful the movie became. Appearing in Forrest Gump would have introduced Dave Chappelle to an extremely large, mainstream audience early on, but the movie isn’t exactly in tune with the tone of his stand-up. A role in a huge movie like this would have been great for Chappelle’s acting career, but it might have proved to be a distraction from his comedy. Chappelle would later play sidekick to Tom Hanks in a dissimilar movie, You’ve Got Mail, in which he didn’t have to portray somebody with a patronizing name like “Bubba.”

2. Rush Hour (1998)

The role: James Carter

Who got it: Chris Tucker

According to IMDb, Dave Chappelle and Martin Lawrence were each considered to play fast-talking LAPD detective James Carter in what became the long-running, lucrative Rush Hour franchise. Like Forrest Gump, Rush Hour would have also introduced Chappelle to a much wider audience, but unlike Gump, this movie had a more comedic role for him that would have allowed him to improvise a significant amount of his dialogue. Still, I doubt Chappelle would have been happy appearing in this series of popcorn movies, had his incarnation of Rush Hour been successful. Dave Chappelle was able to avoid ever taking one of these buddy cop roles that every black stand-up comic-turned actor since Eddie Murphy seems to have to resort to at some point, and he was able to reach the top of his profession without making one.

3. Requiem for a Dream (2000)

The role: Tyrone C. Love

Who go it: Marlon Wayans

In a 2008 interview with Howard Stern, director Darren Aronofsky revealed that Dave Chappelle was his first choice for this part in Requiem for a Dream. Aronofsky says he begged Chappelle to do the movie, but Chappelle turned him down, probably busy with an appearance in the quickly-forgotten Norm Macdonald movie (is there any other kind of Norm Macdonald movie?) Screwed right around that same time.

4. Fletch Won (in development 2003)

The role: Fletch

Filmmaker Kevin Smith spent several years trying to make a third film in Chevy Chase’s Fletch series, developing a reboot that would have replaced Chase with a new, younger actor. While the likes of Jason Lee, Ben Affleck, and Zach Braff nearly ended up in the role, dozens of names were thrown around for the high-profile part. One executive suggested Dave Chappelle for the part, which Kevin Smith called “a stroke of brilliance,” but studio head Harvey Weinstein shot that casting idea down. Had Weinstein been onboard with casting Chappelle in 2003, he would have had a lot of heat on his movie when it came time to release it the following year, with Chappelle’s Show at the peak of its cultural relevancy. Dave Chappelle seems like a much better fit for the part than Zach Braff or anybody else who was in contention for it, but the Fletch prequel never materialized anyway.

For a more detailed look at the casting process for the seemingly-abandoned Fletch reboot, check out this piece I wrote for Splitsider last year.

5. Rick James biopic (in development circa 2004)

The role: Rick James

Dave Chappelle was in talks to play the prolific funk rocker Rick James in this movie based on his autobiography, Memoirs of a Super Freak. Chappelle famously impersonated James on Chappelle’s Show in a sketch that created one of the most irritating, oft-repeated catchphrases in comedy history. Rick James died later that year, but not before telling Chappelle his concerns about the film. James was afraid his children wouldn’t understand the movie, which was apparently supposed to be a comedy. The fact that this was supposed to be a comedy almost makes it sound like it almost would have been like the Chappelle sketch turned into a feature film, which is an odd way to do a celebrity biopic. Chappelle granted Rick James’s wishes for him not to make the movie, though, and a more conventional-sounding Rick James biopic, starring Terrence Howard, went into development a few years later.

6. King of the Park (in development circa 2004)

The role: Charlie Barnett

Charlie Barnett was a stand-up comedian, who frequently performed in public areas like parks and mentored Dave Chappelle in his early days. Barnett never achieved the fame of his peers like Eddie Murphy before dying young of AIDS in the mid-90s, but he was still a wildly popular performer who had a large influence on Chappelle and many others. Chappelle inked a deal to play Barnett in a movie about his life, with Tom Shadyac (Bruce Almighty) directing and Ron Howard and Brian Grazer producing. This was a great opportunity for Chappelle to appear in a role that would have allowed him to perform comedy and drama at the same time, all while paying tribute to his mentor, but Chappelle’s retreat from the entertainment industry in 2005 put the kibosh on this one.

To learn more about Charlie Barnett’s life and legacy, check out this wonderful piece Conor McKeon wrote for Splitsider a few weeks back.

7. Dave Chappelle’s Family History of the World (in development circa 2004)

The role: Himself/various

Writer

Tentatively titled Dave Chappelle’s Family History of the World, a studio executive pitched this feature film comedy to Chappelle, in which he was to “play his family members at various points in history as he chronicles his family’s fictitious involvement in momentous events, from biblical times to the present day, while also riffing on the black experience.” Kind of a modern riff on Mel Brooks’s History of the World Part I. Chappelle, who was to also write the script, was in negotiations to make the movie, but like many of these projects, this one was abandoned when the comedian left Chappelle’s Show and the world of movies and TV in 2005.

8. Judge Paul Mooney (in development circa 2004)

Producer

When Dave Chappelle and his writing/producing partner Neal Brennan renewed their contracts with Comedy Central in 2004, their multi-million dollar deals stipulated that they would create new shows in addition to returning for Seasons 3 and 4. The first of these new shows was a pilot that would have seen Chappelle’s Show regular Paul Mooney doing a humorous version of a TV judge show in which he resolved people’s real disputes. Chappelle calling it quits with Comedy Central stopped this one from going forward, and the network attempted a similar-but-different courtroom series, Root of All Evil, with Lewis Black banging the gavel instead of Mooney.

9. TV shows on NBC and FX (considered in 2004)

Star

With his show at the peak of its popularity at the end of its second season, Dave Chappelle was courted by NBC and FX when it came time to renew his contract with Comedy Central. NBC president Jeff Zucker decided Chappelle was “too expensive,” though, and Chappelle chose Comedy Central’s offer over the also-lofty one FX threw his way.

10. Be Kind Rewind (2008)

The role: Mike

Who got it: Mos Def

Michel Gondry, who directed the concert documentary Dave Chappelle’s Block Party, says that Chappelle was very interested in appearing in his movie Be Kind Rewind. Chappelle even suggested several of the movie remakes contained in Be Kind, including Driving Miss Daisy and Boyz n the Hood. Chappelle ended up unable to make the movie, however, and Chappelle’s Show regular Mos Def slid into his spot instead.

11. Hancock (2008)

The role: John Hancock

Who got it: Will Smith

This unconventional superhero movie spent over a decade in development before it was finally made with Will Smith, but according to IMDb, Dave Chappelle was at one point considered for the lead role. It seems like an ill-fitting part for Chappelle, but, to be fair, Hancock did go through several writers and screenplay drafts during its lengthy development process. The version of the movie that Chappelle almost ended up in might have been quite different from the one we eventually got.

12. Tower Heist (2011)

Unknown supporting role

Another movie that took over a decade to get made, Tower Heist was originally called Trump Heist and envisioned by director Brett Ratner as a “black Ocean’s Eleven.” Ratner signed Eddie Murphy to play the lead role (which eventually went to Ben Stiller) and wanted Chris Rock, Dave Chappelle, and Chris Tucker to play the supporting characters. Ratner was supposedly in talks with this trio of comedians, but he soon decided to turn his idea of a “black Ocean’s Eleven” into a “multiracial but mostly-white Ocean’s Eleven” by sliding Eddie Murphy into the sidekick role and casting Ben Stiller as the lead.

Bradford Evans is a writer living in Los Angeles.