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Bill Hader's 10 Most Iconic Roles

Bill Hader's acting career began in the early 2000s, when he appeared in a few shorts here and there until eventually landing a secondary role in Knocked Up (2007). Since then, Bill Hader has appeared on several movies and TV shows, notably gracing Saturday Night Live with his hilarious sketches and quirky characters.

Most notably and recently appearing in It Chapter 2 and giving the performance of a lifetime, Bill Hader's popularity has really skyrocketed, with many agreeing that he should be a frontrunner for an Oscar this year.

Bill Hader is definitely one talented, hilarious guy. Let's take a look at 10 of his most iconic roles.

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10 VARIOUS - SATURDAY NIGHT LIVE

In 2005, Bill Hader appeared on Saturday Night Live for the first time ever. He would continue appearing in the sketch comedy series until 2013, and in those eight years, Bill Hader was certainly the source of a lot of iconic, internet-famous material.

RELATED: SNL: The 10 Best Skits Of All Time, Ranked

During his time on the show, Bill Hader appeared in countless hilarious sketches, and will definitely be remembered as one of the most notable actors to appear on SNL.

9 BARRY BERKMAN - BARRY

Barry premiered on HBO in 2018, starring Bill Hader in the titular role. Barry has only aired two seasons so far, but it has already received critical acclaim and a significant amount of award nominations. The series is categorized as a dark tragicomedy that revolves around Bill Hader's Barry, a hitman who gets more than he bargained for when he travels to Los Angeles and winds up attending an acting class instead of killing someone.

RELATED: Killing Eve Vs. Barry: 5 Reasons Villanelle Is A Better Assassin (And 5 Why Barry Is)

At the most recent Primetime Emmy Awards, the Barry cast and crew took home three awards, notably including Bill Hader's well-deserved win for Outstanding Lead Actor in a Comedy Series.

8 THE WANDERER - THE DARK CRYSTAL: AGE OF RENAISSANCE

urGoh the Wanderer and The Heretic from The Dark Crystal Age of Resistance

The Dark Crystal: Age Of Renaissance is a prequel to Jim Henson's 1982 film, The Dark Crystal. In the age of remakes, sequels, and prequels, it's unsurprising that a movie notorious for serving as nightmare fuel for countless children would get its own series that further delves into the world originally created in the film.

In this Netflix adaptation, Bill Hader voices The Wanderer, a wise, fittingly comedic Mystic. The role isn't a very major one, but Bill Hader makes it iconic nonetheless.

7 CAPTAIN DOZERMAN - BROOKLYN NINE-NINE

Brooklyn Nine-Nine has definitely featured a creative cast of wacky, iconic supporting and guest characters during its six years on the air, but Bill Hader's character, Captain Dozerman, is easily one of the most unforgettable. Seth Dozerman appears in one episode of the series, and in this episode, Bill Hader gives an absolutely insane, hilarious performer.

RELATED: 10 Relatable Representations of Bisexuality On TV

His character fills the position of Captain after Holt is transferred. Dozerman is quickly revealed to be, well, completely insane, and promptly dies within two days of running the 99th precinct.

6 FEAR - INSIDE OUT

Every character in Pixar's Inside Out is pretty memorable in their own way, being emotions who have emotions, but Bill Hader's portrayal of Fear is one that should not be overlooked. Hader's character is easily the most hilarious in the entire film.

RELATED: 10 Of The Best Pixar Movies, Based On Their Rotten Tomatoes Scores

Fear finds just about every situation, no matter how benign, to be completely terrifying and critically dangerous. Bill Hader encapsulated this character perfectly, and his performance is unforgettable.

5 AARON - TRAINWRECK

Trainwreck was released in theatres in 2015, written by comedian Amy Schumer and directed by Judd Apatow. Amy Schumer and Bill Hader starred in the lead roles, and although this movie is a pretty generic Amy Schumer production, Bill Hader's performance stands out.

He portrays Aaron, a charming, quirky sports doctor. Most likely, if it had been any other actor in this role, the character would have come across as flat and lifeless, but Bill Hader manages to breathe some life and charm into the role.

4 TOM MCDOUGALL - THE MINDY PROJECT

In 2012, The Mindy Project first premiered on FOX, and would later begin airing on Hulu, concluding in 2017 with six seasons. The series was helmed by iconic Mindy Kaling and followed her character's dramatic and often hilarious life.

Bill Hader had a recurring role in The Mindy Project as Tom McDougall, an awkward but morally ambiguous dentist. Tom and Mindy have a rocky relationship, and he ultimately winds up falling in love with a Serbian woman and leaving Mindy. Tom himself was a rather questionable character, but Bill Hader brought enough comedy to the role in order to make the character completely hilarious.

3 MILO DEAN - THE SKELETON TWINS

The Skeleton Twins premiered at the Sundance Film Festival in 2014, starring Kristen Wiig and Bill Hader in opposing roles. The film revolved around the characters, Milo and Maggie Dean, twins who are shown to be having an especially hard time in life, until their struggles ultimately bring them back together as adults.

Both Kristen Wiig and Bill Hader have been praised for their performances in The Skeleton Twins, and rightfully so, as they worked with each other incredibly well and made the film all the more memorable.

2 MICKEY - BOB'S BURGERS

Bob's Burgers is a highly underrated animated sitcom that premiered on Fox in 2011. The series has had quite a difficult run on TV, being cancelled and revived multiple times by various different networks, but was iconic nonetheless.

RELATED: Bob's Burgers: 10 Characters That Could Be Bi

Bill Hader voiced the character Mickey, an awkward, pitiful young man who works as a ride operator at the Wonder Wharf. Mickey appeared sporadically on the show since the second season. The role was fairly minor, but due to Bill Hader's hilarious performance, the character of Mickey is pretty memorable.

1 RICHIE TOZIER - IT CHAPTER 2

Bill Hader and Finn Wolfhard as Richie Tozier in IT Chapter 2

The casting for Andy Muscietti's follow-up to his 2017 smash-hit, It, is often regarded as completely spot-on. The characters in It Chapter 2 were older versions of the iconic Losers' Club, so the cast had to look and resemble the younger actors in a believable way.

Everyone was extremely well cast in this movie, but critics and fans alike have particularly praised Bill Hader for his portrayal of fan-favourite trash mouth Richie Tozier. This was a completely iconic performance, and Hader was undeniably one of the best parts of It Chapter 2, bringing new and charming aspects to the Richie we all know and love.

NEXT: IT Chapter 1 And 2: 10 Moments That Came Straight From The Book

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