There is a very short list of actors who can make you laugh so hard your stomach hurts, and then completely paralyze you with a look of pure, existential dread just one scene later. Bill Hader doesn’t just sit on that list—he might actually top it.
Over the past two decades, the Tulsa, Oklahoma native has pulled off one of the most impressive career evolutions in modern television history. He started as the ultimate utility player on late-night sketch comedy before transitioning into a critically revered, multi-hyphenate creator, writer, and prestige director.
Let’s strip away the impressions and count down the 5 absolute greatest, most defining roles of Bill Hader’s brilliant career.
1. Barry Berkman in Barry (2018–2023)
There is no better place to start than the magnum opus that completely redefined how the industry views Hader’s talent. Co-creating, writing, frequently directing, and starring in HBO’s pitch-black masterpiece, Hader spent four seasons playing Barry Berkman—a deeply depressed, traumatized Midwestern hitman who accidentally falls in love with the theater community while tracking a target in Los Angeles.
Hader’s performance was a masterclass in tonal tightrope walking. He could play Barry as a terrifying, cold-blooded void of violence in one moment, and a desperate, naive child looking for validation in the next. The role earned him consecutive Primetime Emmy Awards for Outstanding Lead Actor in a Comedy Series, permanently cementing him as a premier dramatic heavyweight.
2. Stefon on Saturday Night Live (2005–2013)
Long before he was sweeping the Emmys for heavy drama, Hader was the crown jewel of Studio 8H. While his impressions of everyone from Vincent Price to Alan Alda were legendary, his definitive contribution to pop culture history will always be Stefon, the flamboyant, wildly misinformed New York City city correspondent for Weekend Update.
The true magic of Stefon relied entirely on Hader’s real-time vulnerability. Because writer John Mulaney would famously change the jokes on the cue cards right before the live broadcast, Hader spent half the sketches actively breaking character, covering his face with his hands to hide his laughter. It became an instantly iconic, deeply comforting piece of television history that fans still revisit today.
3. Richie Tozier in It Chapter Two (2019)
Taking over a beloved character established by a younger actor is always a gamble, but Hader stole the entire show in Andy Muschietti’s horror blockbuster sequel. Playing the adult version of the trash-mouthed Richie Tozier, Hader provided the film with its absolute funniest, laugh-out-loud moments of relief against Pennywise the Dancing Clown.
However, Hader did something much deeper with the material. He infused Richie with a profound, closeted heartbreak regarding his unrequited love for his best friend, Eddie. His raw, agonizing grief during the film’s climax was widely hailed by critics as the emotional anchor of the entire horror epic.
4. Milo Dean in The Skeleton Twins (2014)
For industry insiders who assumed Hader could only operate within the safe boundaries of broad comedy, Craig Johnson’s indie darling The Skeleton Twins was a massive wake-up call. Reunited with his longtime SNL castmate Kristen Wiig, the duo played estranged, deeply troubled twins who reluctantly reunite after separately hitting rock bottom.
As Milo, a cynical, gay, out-of-work actor struggling with deep suicidal ideation, Hader was nothing short of magnificent. He brought a sharp, defensive wit to the role that masked an ocean of quiet pain. The film’s iconic, joyous lip-sync sequence to Starship’s “Nothing’s Gonna Stop Us Now” remains a legendary display of the natural, lightning-in-a-bottle chemistry between Hader and Wiig.
5. Officer Slater in Superbad (2007)
You cannot discuss the legacy of 21st-century studio comedies without bowing down to Greg Mottola’s Superbad. While Jonah Hill, Michael Cera, and Christopher Mintz-Plasse anchored the teenage chaos, Hader teamed up with Seth Rogen to deliver the ultimate adult comedic relief as Officer Slater and Officer Michaels.
As arguably the two most irresponsible, unhinged, and hilariously incompetent police officers ever put on screen, Hader and Rogen improvised a vast majority of their scenes. From taking a teenager out to shoot guns to accidentally drifting a police cruiser into a shopping cart, Slater became an infinitely quotable, timeless piece of comedic cinema that helped launch Hader’s big-screen career.
