Top 10 Funniest Sitcom Cameos by Dramatic Actors

Most famous for his roles in westerns, Sam Elliott’s terse demeanor and gravelly voice make him a perfect casting for Ron Dunn, the Eagleton counterpart of “Parks and Rec” regular, Ron Swanson. However, while the two appear similar at first, their differences soon become apparent and hilarious when it’s revealed that Dunn is a hippie, contrasting with Swanson’s more conservative opinions. Despite his differences with his counterpart, Dunn remains an occasional dispenser of wise, if offbeat, advice to several characters on the show during his sporadic appearances.

Given that the show stars Charlie Sheen, it seems only natural for “Two and a Half Men” to have had his father, Martin Sheen, guest star at some point. The elder Sheen, known for weighty dramatic roles in film and TV alike, plays Harvey, the dad of Charlie’s neighbor. At first appearing to be overbearing, Harvey soon manages to romance Charlie’s mother and eventually reveals that he’s every bit as kooky as his daughter is. Sheen’s serious reputation and acting only make Harvey’s absurd turn that much funnier.

In a single guest appearance in the show’s second season, Jonathan Banks portrays Donnie Pritchett, the brother of the family’s patriarch Jay. Contrary to Banks’ reputation for stoic and laconic roles, Donnie is loud and prone to getting into petty, immature fights with his brother. While the role does have some dramatic weight to it, as Donnie reveals to Jay that he has cancer, there’s no getting around how hilarious some of his pranks and other altercations with his sibling are - like that wet willie!

Thanksgiving episodes were usually special occasions on “Friends” and season 8 saw a one-off appearance by Brad Pitt as Will Colbert, an old friend of Ross and Monica’s. Because he used to be heavily overweight and was bullied in high school, Will resented the popular Rachel. This led Will and a reluctant Ross to form an “I Hate Rachel Green” club, while also starting a rumor that she was born with both male and female genitalia. Brad Pitt was married to actress Jennifer Aniston at the time, so seeing him play completely against his real feelings is really funny to see.

Though we considered giving this spot to Matt Damon’s very funny recurring role on “30 Rock,” ultimately we had to go with his singular appearance here. On “Will & Grace,” Damon plays Owen, a man contending with Jack to be in the Manhattan Gay Men's Chorus. Jack discovers Owen is actually straight and seeks to prove it to take out his competition for the spot. Seeing Damon trade shade with Jack is utterly hysterical and we’d have loved to see him do it more.

Though Jon Hamm’s roles are far from humorless, he really gets to stretch his comedic legs with this one. Hamm plays Dr. Drew Baird, a pediatrician and the neighbor of protagonist Liz Lemon, whom she dates. Though quite handsome, Drew is also rather dimwitted and clumsy, only getting by on his good looks. It’s a lot of fun seeing the actor famed for his suave, confident characters play such a lovable doofus; one who’s dumb enough to lose both hands in two separate, yet equally idiotic ways. Liz herself sums him up best: “So handsome…so, so stupid.”

Renowned for his Shakespearean training and weighty dramatic performances, Patrick Stewart is no stranger to comedy, but who knew one of his funniest performances would be as himself! Series protagonist Andy approaches Stewart while working on a production of “The Tempest” in the hopes of getting the actor to help him pitch a script of his. However, Stewart shares an idea of his own, for a story in which he can remove women’s clothes with his mind. And when viewers watch the acclaimed thespian describe his absurd and lewd idea with a straight face, you might then say “you’ve seen everything.”

Famous for his tough and gritty characters, Idris Elba has an equally difficult job in his role on “The Office” – keeping it together opposite the show’s hilarious stars. Elba plays Charles Miner, paper company Dunder Mifflin’s serious vice president, who often acts as the straight man to the antics of the Scranton branch’s workers, finding himself frequently exasperated by their lack of focus on their work. Though usually critical and uncompromising, Charles can also be a bit of a suck up to his own boss, which is a funny contrast with his normal demeanor.

Though he got his start in comedy on film, these days, Michael Keaton is known for his dramatic chops. However, his return to comedic form on “Frasier” is something special. Keaton plays Blaine Sternin, the former brother-in-law of the titular psychiatrist and a reformed con artist apparently turned paraplegic preacher. Blaine’s shady misdeeds and enthusiastic Bible thumping are entertaining enough, but Frasier’s gung-ho attempts to prove that he’s still up to his old tricks lead to some laugh out loud moments; including a rather embarrassing faux pas during Blaine’s sermon.

Before we get to our top pick, here are a few honorable mentions:

Anthony LaPaglia
“Frasier” (1993-2004)

Leonard Nimoy
“The Simpsons” (1989-)

Academy Award winning actor Gary Oldman plays Academy Award winning actor Richard Crosby on “Friends”…er, actually, we meant nominated. Crosby appears opposite Joey in a film in the two part season 7 finale. While his drunken state in the second half is hilarious in its own right, the real crowning jewel takes place in part 1, when Crosby attempts to teach Joey how to be a better actor through over-enunciation and spitting, parodying Oldman’s own distinctive “big” acting style. The duo’s attempts to one-up each other while spraying each other with saliva is absolute comic gold!