Comedy and drama are two different styles of acting and it is incredibly difficult for many performers to do both. Many have tried, but few have succeeded in crossing the boundary. The following list will celebrate thespians who gloriously conquered this challenge.

Five of them were mainly comedic actors with at least one compelling dramatic role under their belt, while the other five were dramatic performers who made people tear up from laughter in a movie once or more. Acting is a difficult craft no matter what the genre. Doing both is a truly monumental achievement and anybody who does it is deserving of the utmost respect.

Comedian To Drama: Robin Williams

The late, great, Robin Williams held a comedic talent no other performer could match. His improvisational skills and his routine on the stand-up stage was hectic and running at a mile a minute. Despite his manic nature, he could also deliver a beautiful dramatic role when the need arose. Roles in films like The World According to Garp, Dead Poets Society, and Good Will Hunting proved his prowess when it came to more serious material.

Dramatic Actor Doing Comedy: Tom Cruise

Tom Cruise is now known as one of the most daring action stars whose starring role in the Mission: Impossible franchise seems to push the edge of what a human body can take for a performance. In his younger days, he took on some serious drama with parts in classics such as Rain Man and Born on the Fourth of July. In 2008, the legendary star took on a surprising role in one of the year’s most daring comedies, Tropic Thunder. In it he plays a foul-mouthed studio executive covered in makeup and barely recognizable.

Comedian To Drama: Jim Carrey

Jim Carrey’s off the wall performances cause audiences of all ages to laugh until they wet their pants. Ace Ventura, Lloyd from Dumb and Dumber, and Stanley Ipkiss from The Mask are just a few of the iconic comedic characters he transformed into for the delight of moviegoers. He also has numerous celebrated dramatic roles under his belt.

Eternal Sunshine of the Spotless Mind and his turn as Andy Kaufman for Man on the Moon showed how he could utilize his talent for more somber stories. While the latter is a biography about a comedian, it still told his life story and its tragic ending.

Dramatic Actor Doing Comedy: Robert De Niro

Robert De Niro performed in several of the most iconic movies of the 1970s, including Taxi Driver and The Godfather Part II. His characters are generally complicated and mean outcasts. While his darker roles are the more celebrated ones, he has also caused people great joy with some comedic parts. The most notable one is Jack Byrnes in Meet the Parents. A more adult-oriented comedic performance can be found in Analyze This, a part which plays on audiences expectations regarding his roles in gangster films.

Comedian Doing Drama: Adam Sandler

Opinions on Adam Sandler vary wildly, though most agree that his comedic output in recent years has been less than stellar. Surprisingly, his most highly-venerated role in over a decade comes from Uncut Gems, a crime drama about the jewel trade.

Before that he co-starred with Don Cheadle in Reign Over Me, playing a man grieving from the loss of his family after the 9/11 terrorist attacks. In the early 2000s, Punch-Drunk Love showed earlier signs of his dramatic abilities. With a track record like this, maybe he should focus his attention more on serious projects.

Dramatic Actor Doing Comedy: Jeff Bridges

Jeff Bridges’ filmography is wide and varied. Rarely can an actor play such a large array of characters and truly blend into it without excess makeup. Few have avoided typecasting the way he has. Despite all this, he seldom performs in comedies. The big exception is The Big Lebowski, a Coen Brothers black comedy following what became cinema’s most iconic stoner. When juxtaposing his laid-back slacker character with the protagonist from True Grit, it is easy to see his immense talent.

Comedian Doing Drama: Marlon Wayans

Hubert Selby Jr’s Requiem For a Dream is one of the harshest literary portrayals of drug addiction and the transmogrification of the American dream. When Darren Aronofsky turned this tragic story into a movie, he needed some top of the line talent to bring the words and characters to life. Most of the cast were already known for drama, with the major outlier being Marlon Wayans, who is more recognizable from In Living Color and White Chicks. Despite this seemingly weird casting choice, Wayans pulls off a magnificent performance.

Dramatic Actor Doing Comedy: Ben Kingsley

Noted thespian Ben Kingsley was hyped up as the Mandarin, Tony Stark’s most noted adversary, for Shane Black’s Iron Man 3. The twist came when the character was revealed as a red herring while the true villain enacted his real plan.

Many were upset by this turn, but Kingsley’s performance as the bumbling idiot ignorant of the grand scheme of things is brilliant. The film, despite its serious themes, is even more comedic than most of the other MCU offerings.

Comedian Doing Drama: Takeshi Kitano

The rest of the world knows Takeshi Kitano for his performances and directorial efforts in Japanese gangster films like Sonatine and Outrage. What many may not know is his established career as one of the funniest people in Japan. For years, his homeland could not take him seriously, reportedly laughing out loud upon his appearance in Merry Christmas Mr. Lawrence. Kitano didn’t give up, however, and is now considered one of the best filmmakers from Japan in the past thirty years.

Dramatic Actor Doing Comedy: Philip Seymour Hoffman

Along Came Polly will sneak up on anybody expecting a run of the mill romantic comedy. Not only does it have the genuine heart of the tired genre, but it also serves up delicious comedy. Philip Seymour Hoffman plays the protagonist’s best friend and comes off as a highlight. It is a far cry from his more noted performances in movies like Capote, but it just goes to show how Hoffman put his all into every role, whether it be an Oscar contender or a run of the mill comedy.

Next: 10 Highest-Grossing Low-Budget Drama Movies Ever Made