Mark Grassick 
Bill Hader is very obviously one of the funniest men on the planet. Whether he’s impersonating Vincent Price or Al Pacino buying a mattress, stealing the show as Amy Schumer’s love interest in Trainwreck, elevating everything from Superbad to Hot Rod with stellar supporting turns, or bringing his inimitable energy to the voice of Flint Lockwood, Hader is never less than totally brilliant. This month, he won an Emmy for his leading role in HBO’s Barry, the story of a hitman who decides to become an actor. It’s surprisingly darker and less silly than expected and is a worthy addition to our list of the SNL alumnus’ best characters. Speaking of which…
STEFON (Saturday Night Live) – There really isn’t anywhere else we could have started. Stefon was a regular highlight on Saturday Night Live’s Weekend Update, mainly due to Hader’s inability to get through a segment without corpsing and Stefon’s irrepressible love for co-host Seth Meyers. His speciality is highly inappropriate cultural recommendations (all of which start “New York’s hottest club is…”) and every single sketch is pant-wettingly hilarious.
VINCENT PRICE (Saturday Night Live) – Another classic. Hader’s voice is ideally placed for the perfect Price impersonation, his left eyebrow is constantly locked at a malevolent angle and the funniest bits stem from his growing exasperation with his unhinged guests (Kristen Wiig as Katherine Hepburn, Jon Hamm as James Mason, Fred Armisen as Liberace).
JOHN SACHS / TREVOR KENNEY / DENVER McIVER (Documentary Now!) – Hader and Fred Armisen’s Documentary Now! may have been a bit hit and miss, but what shines through is their affection for the docs they’re spoofing in each episode. Only once did the satire seem especially savage and that was the season one highlight Dronez: The Hunt For El Chingon. Dronez is a note-perfect takedown of Vice and their cutting-edge hipster journalism, Armisen and Hader playing clueless Americans wandering around Juarez looking for a Mexican drug lord, ignoring all the warnings about their impending deaths.
BOBBY (Adventureland) – Pairing Hader with his former SNL chum Kristen Wiig is a sure-fire recipe for comedy gold. This was immediately evident in the warmly nostalgic coming-of-age comedy Adventureland, where Jesse Eisenberg’s nerd falls for Kristen Stewart while working at a theme park. Hader and Wiig play the park’s managers, and it’s hard not to wish for a version of the movie that centres on these two weirdos, rather than the self-indulgent teens. Bobby charging out with a baseball bat is possibly the highlight of the film. “YOU DON’T KNOW WHAT I’M CAPABLE OF!”
MILO (The Skeleton Twins) – Another pairing of Wiig and Hader, this time as siblings, The Skeleton Twins couldn’t be more different to Adventureland or any of their SNL hi-jinks. If anything in Hader’s career points most obviously to his abilities as a dramatic actor and the dark streak running through Barry, it’s this. He is superb as Milo, Wiig’s gay twin brother who just happened to attempt suicide on the same day that she did. He’s still wonderfully funny, but it’s balanced with moments of true pathos, not least in his scenes opposite his ex-teacher and ex-lover played by Ty Burrell.
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