Top 20 Funniest Sitcom Appearances By Dramatic Actors

“The Simpsons” has a long tradition of celebrity guests. While there are so many to choose from, our pick goes to Mr. Spock himself, Leonard Nimoy. The late “Star Trek” icon appears in the famed episode, “Marge vs. the Monorail,” as himself. Nimoy helps announce Springfield’s ill-advised monorail, and is mistaken for someone else by the mayor. While taking a trip on the town’s new transportation system, Nimoy saves the life of Krusty the Clown. Although his comments on the solar eclipse aren’t appreciated by his fellow passengers, we enjoy them. And if his disappearance at the end of the episode is anything to go by, Mr. Nimoy’s presence may be more important than they realize.

George Costanza is always eager to stand out, so when a used car salesman offers him a car that supposedly belonged to Jon Voight, he jumps at the chance. However, despite his love of the LeBaron and its contents, including a chewed up pencil, some things don’t add up - like the spelling of the previous owner’s name. However, a new opportunity arises when his friend Kramer runs into Jon Voight on the street. Kramer chases the actor down, only for Voight to bite him! And while we’d get that tested, Kramer and George hatch a scheme to compare the teeth marks on the pencil to those on Kramer’s arm! It’s a short, but hilariously “biting” cameo!

Anthony LaPaglia may be known primarily for appearing in crime dramas, but one of his most acclaimed roles was in this sitcom. The Australian actor appears in a recurring part as Daphne Moon’s brother, Simon. An odious lech who’s inexplicably popular with women, Simon is an occasional visitor to Seattle, where he makes himself an unwanted guest of Niles and Frasier Crane. While he may drive the Crane brothers, and his sister, up the wall, Simon is a wildly entertaining character. He’s funny enough that LaPaglia’s performance earned him an Emmy award.

We’ll forgive you if you fail to recognize that Edward Norton is even in the show, since he’s borderline unrecognizable in this role! In the first season, Claire Dunphy decides to get her husband Phil an anniversary present - a singer from his favorite band. The singer, Izzy LaFontaine, is played by Norton, who has a ridiculous hairstyle and goatee, not to mention an English accent. However, it turns out that Phil has never heard of LaFontaine’s band, and that their song is something else entirely. Nevertheless, husband and wife are brought closer together, and we’re treated to a great Ed Norton comedic cameo.

Charlize Theron is an Oscar-winning actress known for dramatic and action-oriented films. But her turn on the small screen in a comedic part is great, too. She makes several appearances in “Arrested Development”’s third season, playing Rita Leeds. Rita is a quirky British woman, whom Michael falls for, and, surprisingly, manages to date. The rest of the Bluth family suspects her of being a spy. However, the truth is a little different. Playing someone with lower than average mental faculties can be very tricky, but Theron’s turn as Rita is adorable, sweet, and quite funny.

As a veteran actor, Michael Douglas has all kinds of range, but comedy from him is not as common. So it was a real treat when he appeared on “Will & Grace.” Douglas plays Gavin, a detective who assists Will in finding his missing laptop. However, Jack learns at a support group that Gavin lied to Will to get closer to him, since he came out later in life and isn’t comfortable asking men on dates yet. Between his and Will’s “undercover” time at a gay bar, and Will eventually getting the truth out of him, Douglas’s performance is pure comedy joy.

While Bruce Willis is known as an action star, most of his work also involves at least some comedy. He certainly works those familiar muscles on “Friends.” Willis plays Paul Stevens, who is the father of Elizabeth, the college student Ross is dating. In just a few episodes, Willis really shows his range, going from the overprotective father to letting his emotions out - maybe a little too much. The easy highlight of his time on the show though is Paul’s pep talk to himself in the mirror. Whether you think he’s a love machine or not, Bruce Willis is definitely “the man.”

When the rest of his friends go to Comic-Con without him, Sheldon Cooper is determined to start his own convention - with James Earl Jones as a guest. While Sheldon’s luck with celebrities usually ends with a restraining order, Jones actually hits it off with Sheldon. The two spend the night hanging out. After dinner, karaoke, and pranking Carrie Fisher, the duo ends up in a sauna. Jones does a great job playing an exaggerated version of himself. Although his tendency to pontificate does end up annoying Sheldon by the end of the night, we’d gladly trade places with him!

Colin Farrell has excellent comedic chops, even if many of his roles are in dramas. The Irish actor plays Billy Callahan, a man who accompanies a patient to Sacred Heart Hospital. He’s immediately popular around the hospital, both for his carefree attitude, and way with women (and Todd). However, it eventually comes out that Billy got in a bar fight with the patient in question, and he stuck around out of responsibility. Although J.D. and Turk are obligated to report him to the police, Billy forgives them - even if the rest of the staff don’t.

While we were tempted to include Sterling K. Brown’s appearance, we ultimately elected for J.K. Simmons instead, since his role is more traditionally funny. Simmons plays Detective Dillman, an old colleague of the 99th precinct’s captain, Raymond Holt. Brought in to solve a whodunnit prank, Dillman immediately proves hypercompetent, if overly serious. His ability to know everything about someone from a single response is absurd. However, he ultimately frames Jake for the crime, hoping to get recommended for a task force. Jake exposes him… and the fact that he’s working at Yarn Barn. Simmons brings a hilarious deadpan energy to the role, and we just wish “Brooklyn Nine-Nine” had doubled-back on this character.

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 - his guest spot on “Frasier” was also a contender for our list! Still, 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” was 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.

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!

What’s your fave comedic turn by a dramatic actor? Let us know in the comments!