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Why 'Pinball' Parker From Con Air Looks So Familiar

Producer Jerry Bruckheimer was on an absolute tear in the mid '90s. In 1995 alone, he worked on director Michael Bay's buddy-cop thriller "Bad Boys" — which established Will Smith as a bona fide action star — Tony Scott's tense naval submarine drama "Crimson Tide" — which reminded audiences how talented Gene Hackman and Denzel Washington are — and "Dangerous Minds," starring Michelle Pfeiffer, which introduced the world to rapper Coolio via its soundtrack and his enduring single "Gangsta's Paradise." A year later, Bruckheimer teamed up with Bay again for the over-the-top action thriller "The Rock," which gave the world it's erstwhile least-likely action star — a title now reserved for Bob Odenkirk in "Nobody" — in Nicolas Cage. Then 1998 saw another Bay collaboration for the Bruce Willis disasteroid flick "Armageddon" and another team up with Scott for "Enemy of the State," another action thriller for Smith, with Hackman aboard as well. This slate of films featured a lot of common factors, as you can see, and smack in the middle the stars aligned for Bruckheimer to work on another over-the-top action thriller starring Cage: 1997's "Con Air."

A good chunk of the movie takes place aboard the titular aircraft, a Department of Corrections plane crewed by United States Marshalls and used to transport the worst criminals in the history of prison movies. Cage stars as Cameron Poe, a former Army Ranger who's been behind bars for years after killing a man in self defense. But he's just catching a ride home. The big fish are Cyrus "The Virus" Grissom (John Malkovich) and Nathan "Diamond Dog" Jones (Ving Rhames), who engineer the prison plane's hijacking that forms the movie's premise. Helping them out is a "two-bit" crackhead — Grissom's words — named Joe "Pinball" Parker, whose job it is to cause a distraction and get Grissom and Jones free of their cells. The character should easily be recognizable and actor and comedian Dave Chappelle. Here's why "Pinball" from "Con Air" looks so familiar

He played Ahchoo in Robin Hood: Men in Tights

Dave Chapelle's first credited acting role came working alongside a comedy legend. In 1993, writer, director, actor, and comedian Mel Brooks set his sights on a tale told many a time: the legend of Robin Hood. Brooks' penchant for parody and satire often came with a specific target in mind — 1974's "Young Frankenstein" mocked the monster movie genre as a whole, while 1987's "Spaceballs" was primarily aimed at the sci-fi mythology of the then-young "Star Wars" franchise — which in the case of "Men in Tights" was most likely 1991's Kevin Costner-starring "Robin Hood: Prince of Thieves," which may have taken itself way too seriously. Fortunately, Mel Brooks didn't take it seriously at all.

Chappelle provides plenty of laughs as Ahchoo, the right-hand man to Cary Elwes' Robin of Loxley. Robin has agreed to look after the young Ahchoo after his father, Asneeze (Isaac Hayes), helps him escape from prison during the Crusades with a great feat of strength, which was actually great strength of feet. Upon returning to his beloved England, Robin happens upon Ahchoo, as he's being harassed by the Sheriff of Rottingham's (Roger Rees) men, a scene in which Ahchoo asks for a break because he's "running out of air" and then uses the brief respite to re-inflate his Reebok Pumps. Ahchoo is also responsible for delivering the immortal line "Pissed off? If I was that close to a horse's wiener I'd be worrying about being pissed on!" to the angry sheriff, whose broken saddle has inverted him to a position straddling his horse's stomach. Ahchoo, upon Robin naming him the new sheriff at the end of the film, also reminded the surprised townspeople that "Blazing Saddles," another Mel Brooks movie, also featured a black sheriff.

He made a brief appearance in the first Nutty Professor movie

After "Men in Tights," Dave Chappelle appeared in the short-lived sitcom "Buddies" in 1996. The show, which only aired five of the 13 episodes that were produced, was actually based on his guest appearance with comedian Jim Breuer on an episode of "Home Improvement," though Breuer was replaced by actor Christopher Gartin for "Buddies." Chappelle later said he knew the show was doomed even while it was in production, telling CBS News, "It was a bad show. It was bad. I mean when we were doing it — I could tell this was not gonna work."

Fortunately, Chappelle managed a quick rebound with an appearance in the first "Nutty Professor" movie. The film offered him the chance to work with another stand-up comedy legend in Eddie Murphy, who played the title character, Professor Sherman Klump, and his skinny but downright mean and evil alter ego, Buddy love — that's in addition to playing most of the Klump family, seven characters in all. Chappelle appears as stand-up comedian Reggie Warrington, whose brutal insults initially inspire Sherman to come up with his troublesome weight-loss solution. When Buddy is out for a night on the town, he pays Reggie a visit and the fictional funny man soon becomes Buddy's unwitting target, as does his absent mother, who is used as the butt of a string of fat jokes; after all, who better to drop a bunch of zingers about overweight people than a character who was, until recently, morbidly obese. Unhappy about being upstaged, Reggie challenges Buddy to some fisticuffs and is quickly outmatched. 

Chappelle recalled working on the film during an interview with Inside the Actor's Studio (via Genius), saying "I'm walking on the set ... this fat dude comes up like, 'Hey, man, you're real funny.' I'm like 'Thanks.' ... It was Eddie Murphy, he had that makeup on, and he knew my jokes. He started telling obscure jokes I did, like he knew 'em," Chapelle said fondly.

Dave Chappelle played Thurgood in the stoner classic Half Baked

Despite Jim Breuer's role being recast on "Buddies" and the failure of the show as a whole, he and Dave Chappelle would go on to collaborate for 1998's stoner comedy cult classic, "Half Baked." Chappelle's character, janitor Thurgood Jenkins, and Breuer's, a burnt-out record store employee named Brian, comprised half of a quartet of childhood friends who grew up smoking weed together and now share an apartment in New York City. Joining them were Guillermo Díaz's hot-tempered fast-food worker, Scarface, and Harland Williams as school teacher Kenny. When Kenny goes on a snack run and accidentally kills a diabetic police horse by feeding it the junk food he's supposed to bring back to his friends, the remaining three must rally together to raise money for his bail before he's eaten alive behind bars. As it happens, Thurgood pushes a mop at a lab with pharmaceutical-grade cannabis. So a stoner who needs cash has access to powerful drugs; unless you're high, you can see where this is going. 

In addition to its talented main cast, "Half Baked" featured a ton of cameos as well. Chappelle's character delivers weed to former "Daily Show" host Jon Stewart and gets into a verbal altercation with Bob Saget of "Full House" fame when he goes to a meeting for addicts and is mocked for claiming to be hooked on marijuana. Snoop Dogg shows up as an opportunistic scavenger smoker, the type of guy who's always down to share a joint, unless it's his own.

Critics panned "Half Baked" and the film has a lowly 29% critics score on review aggregator Rotten Tomatoes. The film grossed a bit less than $17.5 million worldwide, according to Box Office Mojo, though it still resonates with audiences of a certain persuasion.

Chappelle starred in Screwed alongside SNL alum Norm MacDonald

Not content to star in just one ill-received comedy about a harebrained scheme alongside a talented "Saturday Night Live" player, Dave Chappelle teamed up with Norm MacDonald for 2000's bomb-com "Screwed." MacDonald plays a down-on-his-luck chauffeur named Willard Fillmore, whose unbearable boss, Mrs. Crock (Elaine Stritch), doesn't appreciate him and didn't appreciate his father before him, but of course lavishes gifts upon her boyfriend and dog. Willard and his chicken restaurant-owning best friend, Rusty P. Hayes (Chappelle) hatch a scheme to kidnap the dog and hold it for ransom. Shockingly, that plan goes wrong and the cops think Willard is the one who was kidnapped, while the public pressures Mrs. Crock to pay the nonexistent ransom demands, which leads to another scheme, one that requires a dead body and the help of mortuary work Grover Cleaver (Danny DeVito) — the third character with a name vaguely referencing a United States president, none of which is ever really explained.

"Screwed" performed even worse with reviewers than "Half Baked," managing a pitiful 10% critics score on Rotten Tomatoes and prompting absolute savagery from critics. Variety reviewer Joe Leydon called the movie "latenight cable TV filler disguised as a feature film," and Film.com's Tom Keogh opined "If this is how they want to squander a hard-earned opportunity, they should keep their day jobs."

He created his own eponymous sketch series, Chappelle's Show, for Comedy Central

Dave Chappelle is, perhaps, most easily recognizable from his eponymous Comedy Central sketch show, "Chappelle's Show," though, at times, he was able to disappear entirely into the characters he took on for the show. Chappelle's "Half Baked" co-stars Jim Breuer and Guillermo Diaz made appearances on the show, though the guest star to appear most frequently was the late Charlie Murphy — brother to Chappelle's "Nutty Professor" co-star Eddie Murphy — whose most memorable sketches were "Charlie Murphy's True Hollywood Stories." In the aforementioned sketches, Charlie Murphy is slapped by musician Rick James and loses a game of pick-up basketball to legendary musician Prince, with Chappelle playing both James and Prince in the respective bits. The best part: both instances were, indeed, true Hollywood stories. James confirmed the slapping story in interview footage produced for the skit. Prince confirmed the basketball story in brief to MTV, though it received more substantial confirmation recently.

"That is totally and absolutely accurate," Eddie Murphy confirmed to late night host Jimmy Fallon in February while promoting "Coming 2 America." "My brother was like, 'Alright, it's going to be shirts against blouses.' And the blouses won, they beat the s*** out of us. We had one dude on our squad that could play, named Larry, and he didn't have no shoes, so Prince gave him some sneakers. And Prince wore like two, three sizes smaller than Larry, but Larry was so excited to have Prince's sneakers on, he put those tiny sneakers on his feet, so he couldn't do his game right."