The achievements of comedians who have made impressive transitions from comedy to drama have been well documented in recent years. Be itAdam Sandler’s performance inUncut Gems,Jim Carrey’s many examples of dramatic brilliance throughout his career, or, of course, the Oscar-winning talentRobin Williamsuncovered when he turned his attention to more serious roles. But what about those who have made the opposite transition?

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A delicate art of timing, nuance, and perfect delivery, comedy is difficult to learn and almost impossible to master without some semblance of natural talent in the field. Yet these acclaimed actors, thespians in the truest sense of the word, have shown on multiple occasions that they have a prowess for comedy which has repeatedly left audiences howling with laughter.

George Clooney

Best known for the effortless charisma he brings to many of his roles, it’s easy to forgetGeorge Clooneyis one of the most multi-talented individuals in Hollywood. He’s been nominated for Academy Awards across six categories (the second most of anyone in film history) and won Best Supporting Actor in 2006 for his performance inSyriana.

Becoming an A-lister in the 90s after starting inER, Clooney brought a comedic undertone to many of his characters, but it wasn’t until he appeared inThe Coen Brothers’O Brother, Where Art Thou?that the depth of his comedic talent was put on show. Through frequent collaborations with the Coens, and performances in such films asThe Men Who Stare At Goats, Clooney’s excellence in offbeat comedy has become a key pillar to his celebrated career.

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WhileBrad Pitt’s breakout role came inRidley Scott’s comedyThelma & Louise, it wasn’t until his dramatic performances in films likeLegends of the Fall,Interview With A Vampire, andSeventhat he started to establish himself as an A-grade actor. While he flirted with his comedic flare a number of times through the early 2000s, it was his performance inBurn After Readythat showcased his talent in the genre.

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While he hasn’t re-visited the genre to that extent since, he’s still showcased his knack for comedic timing in many of his performances. From his darkly hilarious roles inQuentin Tarantino’sInglourious BasterdsandOnce Upon A Time in Hollywood, to his idiosyncratic General inWar Machine, his comedic indulges have been a delight for fans everywhere.

Morgan Freeman

With a career spanning as far back as 1964,Morgan Freemanis one of the most famous, beloved, and acclaimed actors of all time. With his world-weariness, casual charm, and that glorious voice, he’s played prominent roles in some of America’s greatest films and been nominated for five Oscars along the way, winning one for his performance inMillion Dollar Baby.

One of his first notable forays into comedy came in 2003 when he appeared as God inBruce Almighty. He displayed he had the deft touch to excel in the genre which he has exhibited again many times since in films likeThe Bucket List,Going In Style, andLast Vegas.

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Alan Rickman

Whether he was holding Nakatomi Plaza hostage, coming at odds with Robin Hood, or scorning Harry Potter and his friends,Alan Rickmanwasutterly flawless in the many villainous roles he played. While he also earned acclaim for his performances in numerous English dramas, one aspect of his illustrious career which hasn’t been as celebrated as it ought to be is his brief but hilarious stint in comedies.

In 1999, he played big parts inDogmaandGalaxy Questwhere, while he maintained his trademark stoicism, his gift for comedy stole the show. He carried on the trend in the early 2000s with smaller roles inLove ActuallyandA Hitchhiker’s Guide to the Galaxy, both of which exemplified his brilliant timing and delivery.

M. Gustave smiling at the camera in The Grand Budapest Hotel

Ralph Fiennes

From playing Amon Göth inSchindler’s Listto Lord Voldemort in theHarry Potterfilms,Ralph Fiennesis best known as one of the most imposing villainous actors in modern Hollywood. Even in his appearances as a protagonist, he occupies the screen with a commanding presence, which has made seamless shift into comedy all the more intriguing.

While he remained an intimidating figure in 2008’s black comedyIn Bruges, it was his performance inThe Grand Budapest Hotelwhich saw him make a complete transition to the genre. Fiennes has remained active in comedy since, with appearances inHail, Caesar!,Holmes & Watson,The Menu, and his upcoming role inWes Anderson’sThe Wonderful Story of Henry Sugar.

Meryl Streep in The Devil Wears Prada

Meryl Streep

With the absurd world record of 21 Academy Award nominations (winning three of them),Meryl Streepis arguably the greatest actor to have ever graced the screen. Her acclaimed performances throughout her career are too many to count, but she has become renowned for the sheer versatility she has displayed in her Oscar-winning performances inKramer vs Kramer,Sophie’s Choice, andThe Iron Lady.

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That versatility has even worked in comedy, with Streep regularly proving herself to be an astute comic in multiple roles through the 21st century. Among the most iconic and quotable of those was her portrayal of Miranda Priestly inThe Devil Wears Prada, a role which earned her one of her Oscar nominations. She then starred in the musical rom-comMamma Mia!and its sequel before offeringa scene-stealing performance in 2021’s political satireDon’t Look Up.

Robert De Niro

Immortalized as one of Hollywood’s greatest ever actors, there isn’t much thatRobert De Nirohasn’t done. While he’s probably best known for his tough-guy roles in movies likeThe Godfather: Part IIandGoodfellas, he has shown brilliance in more comedic roles as well.

He made his first real foray into comedy with 1997’sWag the Dogwhich kick-started a string of comedic roles for him through the late 90s and early 2000s. He was hilarious inAnalyze ThisandMeet the Parentsand has appeared in a wide variety of comedies since, fromThe FamilytoSilver Linings Playbook, and even films likeGrudge MatchandDirty Grandpa.

Edward Norton

Breaking out with his film debut inPrimal Fearin 1996 before finding further acclaim inAmerican History XandFight Clubin the late 90s,Edward Nortonimmediately stamped himself as an actor to be taken seriously. That reputation goes deep ifrumors of infighting on the set ofThe Incredible Hulkare to be believed, which makes his exceptional comedic performances all the more remarkable.

He directed and starred in the romantic-comedyKeeping the Faithin 2000 before appearing inDeath to Smoochyin 2002, but it wasWes Anderson’sMoonrise Kingdomwhere Norton’s comedic talent really came to fruition. He’s worked with Anderson another three times since, offering the perfect slice of offbeat humor to the director’s quirky comedies, and earned an Oscar nomination for his hilarious performance inBirdmanor (The Unexpected Virtue of Ignorance).

Emma Thompson

It’s not an overstatement to describeEmma Thompsonas one of the finest actors of her generation. She became a star in the 1990s with winning an Oscar for her performance inHowards Endwhile garnering acclaim in such films asThe Remains of the Day,In the Name of the Father, andSense and Sensibility, which she earned her second Oscar for as the screenwriter.

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While her wit was almost always on display, it wasn’t really untilLove Actuallyin 2003 that Thompson begun to show the full extent of her comedic prowess. A hallmark of many of her comedy roles is they’ve still allowed plenty of room for her to showcase all her acting talent, as was the case inStranger Than Fiction,Late Night, and her recent releaseGood Luck to You,Leo Grande.

Dustin Hoffman

Among the most chameleonic actors Hollywood has ever seen, there are few genresDustin Hoffmanhasn’t garnered critical acclaim in. While best known for his many dramatic exploits, including his Oscar-winning performances inRain ManandKramer vs Kramer, Hoffman has an undeniable gift for comedy which he has showcased regularly throughout his career.

He earned two of his seven Academy Award nominations for his performances in comediesTootsieandWag the Dogbefore appearing in broader comedy hits likeMeet the Fockers,Stranger Than Fiction, andThe Meyerowitz Stories. Sometimes a deadpan cynic, other times an over-exuberant delight, Hoffman’s numerous comedy roles have given audiences plenty to laugh at.

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