The 20 best and craziest roles of Bill Hader’s career

Although he has been acting in film and TV since 2005, Hader didn’t have a true leading role until the 2015 Amy Schumer comedy “Trainwreck,” in which he played Dr. Aaron Conners, the love interest of Schumer’s character. Seeing Hader as a doctor who is best friends with LeBron James was a bit of a stretch at first. But after finding out the surgeon’s favorite song is Billy Joel’s “Uptown Girl,” we knew he was a perfect fit in the unique role, which earned the comedian a Critics Choice Award nomination.

Barry Berkman is a character unlike any other Bill Hader has ever played. He’s a Midwestern hitman who travels to Los Angeles for a job but ends up discovering he has acting aspirations. The HBO series debuted on March 25, 2018, received positive reviews, and was renewed for a second season less than three weeks later. Hader stars in “Barry” alongside Stephen Root, Sarah Goldberg, Glenn Fleshler, Anthony Carrigan and Henry Winkler. Hader is also a creator and executive producer of the show.

BB-8 isn’t really a crazy character; what’s nutty is that Bill Hader provided the voice for the Star Wars droid — a fact few people are aware of. After Hader initially recorded the voice, J.J. Abrams and the effects team figured out the best sound result came from putting Bill’s voice through a talk box (the unit that Peter Frampton made famous). Hader received a credit in “Star Wars: The Force Awakens,” he says, for about an hour’s work.

When Bill Hader appeared in the season three premiere of “Brooklyn Nine-Nine,” we were ecstatic but had a couple questions. How long would he stay? And what would happen to the former leader, Capt. Holt (Andre Braugher)? Although we’d have to wait a few episodes for the answer to the second mystery, the first was solved almost immediately, as Capt. Seth Dozerman (Bill Hader) comically died of a heart attack in the very same episode in which he was introduced. Oh well, he had a good run, but also an aortic valve that was just too narrow.

When Rod Kimble (Andy Samberg) needed support for his big motorbike jump in 2007’s “Hot Rod,” he enlisted his half-brother Kevin (Jorma Taccone) and friends Rico (Danny McBride) and Dave (Bill Hader). In addition to his stoner-esque humor, Dave is mostly remembered for the scene toward the end of the film where he trips hard on acid, gets a piece of metal stuck in his eye and ends up giving important advice to Rod on the way to the hospital.

“Cloudy with a Chance of Meatballs” is a veritable who’s-who of famous actors and comedians — including Anna Faris, James Caan, Neil Patrick Harris, Andy Samberg and Bruce Campbell — but Bill Hader anchors them all in the 2009 sci-fi adventure comedy as inventor and protagonist Flint Lockwood. Of course, because it’s Bill Hader, the actor isn’t limited to a single role; he also voices the Flint Lockwood Diatonic Super Mutating Dynamic Food Replicator invention, or “FLDSMDFR.”

An all-star cast was enlisted to portray various historical figures in 2009’s “Night at the Museum: Battle of the Smithsonian,” including Robin Williams as Teddy Roosevelt, Amy Adams as Amelia Earhart, Christopher Guest as Ivan the Terrible, Jon Bernthal as Al Capone and Bill Hader as Gen. George Custer. Of course Hader’s impression is on point, but we also enjoyed his appearance in this sequel because he had some genuinely funny bits, including the one where he can’t pronounce Sacagawea’s name. Sure, the whole thing was a bit corny, but it’s a kid’s movie, so let’s lower our expectations a bit.

The idea behind the original character of Herb Welch is simple: he’s a curmudgeonly old man who speaks in deadpan, a field reporter for WXPD News who constantly hits people in the face with his microphone during interviews. Yet somehow this limited formula worked, and it wasn’t uncommon to see Hader play Welch in one of the first post-monologue sketches of the night on numerous occasions. And why not? There’s no shortage of skip-worthy “SNL” content nowadays (sorry, NBC), but Herb Welch is definitely worth a watch each time.

In addition to Hader’s numerous regular characters and impressions on “SNL,” he also had some memorable one-offs, including his potentially disastrous role as an electric-wheelchair-bound old man named Horace in a season 43 sketch. In it, a woman (Cecily Strong) brings her elderly husband (Hader) to game night with three of her girlfriends (Heidi Gardner, Aidy Bryant and Melissa Villaseñor) and things get uncomfortable. Toward the end, Strong’s character decides to storm out while sitting on Hader’s lap. Not only does she barely manage to stay on the moving wheelchair, but Hader accidentally backs up into a set of chairs and a table, inadvertently taking Villaseñor with him, and causing the entire cast (Hader included) to break into stifled laughter.

It’s hard to pick one role of Bill Hader’s that stands out in “Documentary Now!” because he plays at least one new character in each episode. For this list, we’ll go with his role as aging socialite and recluse Little Vivvy in the impeccable spoof of “Grey Gardens” entitled “Sandy Passage.” Hader later said he didn’t think he and Fred Armisen dressing in drag was a good idea because of all the talented female comedians out there. But in the end, the show is really about him and Armisen tackling every major role, and we’re glad he reconsidered.

Mickey’s a great guy. He’s kind, funny, good with kids and always willing to lend a helping hand. He also happens to be a convicted bank robber, a weak-legged pedicab driver, and a negligent theme park ride operator, but we won’t hold that against him. Mickey made his “Bob’s Burgers” debut in the season two episode “Bob Day Afternoon,” where he gets busted trying to steal from the bank across the street from the Belcher’s restaurant but avoids his biggest fear: having his pants falls down during the arrest.

In a departure from his usual comedic roles, Bill Hader shows he has some dramatic chops in the 2014 Craig Johnson dramedy “The Skeleton Twins.” The script (which won the Waldo Salt Screenwriting Award at Sundance) uses dark humor to balance out the heavy subject matter that includes depression, suicide and infidelity — and Hader and Kristen Wiig were the perfect actors to pull off this feat. Most memorably, the co-stars lip-sync to Starship’s “Nothing’s Gonna Stop Us Now,” a scene that earned a nomination for Best Music Moment at the 2015 MTV Movie Awards.

We enjoy trying to spot and guess celebrity voices in commercials, so imagine our delight when we heard Bill Hader’s voice coming out of Mr. Peanut in a variety of Planters ads beginning a few years ago. Interestingly, Hader doesn’t really do a “voice” for the character, opting instead to use his normal voice, which actually works quite well for the monocle- and top hat-wearing spokesnut. The funniest part of the role, however, is the fact that in real life, Hader is allergic to peanuts.

In Judd Apatow’s 2007 comedy “Superbad,” 17-year-old McLovin (Christopher Mintz-Plasse) goes for a ride with a pair of crazy cops played by Seth Rogen and Bill Hader. The trio chase bad guys, crack jokes, chug beers, shoot guns and end up torching their patrol car ... all while Officer Slater (Hader) is the senior officer.

As an admittedly anxious and easily embarrassed person, Bill Hader doesn’t seem like the type to participate in a roast, as he’d have to stand up in front of an enormous audience and cruelly diss his fellow celebrities — some of whom are more famous than he is. This explains why, at the Comedy Central Roast of James Franco, Hader appeared in character as the “President of Hollywood,” a fictional executive that personifies the entire city and showbiz industry. Hader had some hilarious lines, including, when poking fun at Seth Rogen’s new film “The Guilt Trip” with Barbra Streisand: “Listen, if I wanted to watch two ugly jews weaving through traffic, I’d watch Seinfeld’s web series.” This character was later adapted into Jerry Wallach, a fictional Hollywood legend who was the focus of the last two episodes of season two of “Documentary Now!”

With apologies to the stars of “Pineapple Express,” Seth Rogen and James Franco, but we still think the funniest scene in the film is the very first one. In an underground army bunker in 1937, a private (Hader) is given a joint as part of an experiment. He becomes humorously euphoric and begins criticizing the “little dog and pony act you call a military.” The project is immediately shut down by the commanding officer, marijuana is made illegal, and the film begins in 2008 with no relation to the opening scene.

Is Bill Hader’s role in the 2008 comedy “Tropic Thunder” necessary? Not at all. In fact, even his boss, Les Grossman (Tom Cruise), tells him a monkey could do his job. That being said, we could watch the clip of him dancing behind Grossman to Flo Rida’s “Low” on repeat for the rest of eternity.

During his time on “Saturday Night Live” as a cast member and a host, Bill Hader occasionally played the character of Stefon. Stefon became iconic as a flamboyant Weekend Update correspondent who was supposed to give travel trips to tourists but instead described New York’s hottest new clubs —  always involving bizarre names, sketchy settings, and questionable owners, employees, and patrons. The bit was so side-splittingly hilarious that Hader often couldn’t control his laughter (and had to cover his face to hide this fact), part of which was due to the fact that comedian and former “SNL” writer John Mulaney would change or add random lines just before showtime.

If you’re not a huge Bill Hader fan, you might not have known the actor has credits in both a Star Wars film (as previously mentioned) and a Star Trek film. In the 2013 sequel “Star Trek Into Darkness,” Hader provided the voice of the computer on the USS Vengeance, the Starfleet combat ship helmed by Admiral Alexander Marcus and later overtaken by Khan. Viewers who understandably got sucked into the story would probably miss the comedian’s audio cameo. But for audience members playing close attention, the voiceover is hard to miss and clearly Hader.

With the multitude of impressions perfected by Bill Hader during his time on “Saturday Night Live” (including Al Pacino, James Carville, Alan Alda, Charlie Rose and Clint Eastwood) it’s difficult to pick the best, so we’ll go with our favorite, Vincent Price. Perhaps it’s because we already adore the horror legend, or maybe it’s just because Hader totally nails it, but we’ve always been fans of this impression and will regularly go back and watch the old Variety Vault sketches because of it. Interestingly, Hader says he only did impressions of friends, family members and teachers prior to his acting days, and he didn’t start impersonating celebrities until he joined “SNL.”