In the modern history of screen comedy, few transitions have been as staggering to witness as the artistic evolution of Bill Hader.
For eight unforgettable seasons on Saturday Night Live, Hader was late-night television’s undisputed utility ace: an impressionist wizard and character dynamo capable of rescuing sketches with an eccentric glance, a maniacal laugh, or hands trembling over his face as weekend club kid Stefon.
Yet behind the breathless mimicry lived an obsessive cinephile and visual storyteller. In creating, directing, writing, and starring in HBO’s Barry, Hader shattered the boundary between prestige comedy and harrowing psychological thriller, earning multiple Primetime Emmy Awards and establishing himself as one of Hollywood’s most visionary auteur filmmakers.
Here are the 10 best Bill Hader movies and TV shows, ranked from great to transcendent.
10. Forgetting Sarah Marshall (2008)
The Role: Peter Bretter's supportive, exasperated stepbrother who dispenses marital realism and awkward breakup advice over glitchy video calls.
In Nicholas Stoller’s beloved Hawaiian breakup comedy, Hader steals every scene he appears in despite being geographically isolated in an apartment on the mainland. His deadpan webcam reactions to Jason Segel’s emotional breakdowns—complete with freezing screens, lagging audio, and earnest fraternal love—ground the romantic absurdity in relatable domestic charm.
9. Cloudy with a Chance of Meatballs (2009)
The Role: An overly enthusiastic, socially isolated inventor who accidentally causes food to rain from the sky over his small island town.
Phil Lord and Christopher Miller’s directorial breakthrough showcased Hader’s exceptional voice-acting brilliance alongside longtime Studio 8H castmate Andy Samberg. Infusing Flint Lockwood with boundless, caffeinated scientific optimism and deep yearning for his father’s approval, Hader carried the frantic, visually inventive comedy with pure, lovable sincerity.
8. Trainwreck (2015)
The Role: A nerdy, gentle sports orthopedic surgeon who falls in love with a commitment-phobic magazine writer.
Trainwreck demonstrated that Hader had the emotional vulnerability to step into romantic leading-man shoes. Acting opposite Amy Schumer and long-time SNL collaborator Vanessa Bayer, Hader played Dr. Aaron Conners with zero cynicism, offering a sweet, grounded presence and sparking hilarious comedic chemistry with LeBron James.
7. Tropic Thunder (2008)
The Role: A terrified junior studio executive forced to dance, grovel, and placate Tom Cruise’s psychotic mega-producer Les Grossman.
Ben Stiller’s biting satire of Hollywood ego and war filmmaking featured an ensemble stacked with comedic heavyweights. Yet Hader carved out a permanent legacy as the spineless executive Rob Slolom. His physical terror standing beside Tom Cruise’s foul-mouthed Grossman—nervously nodding along to hip-hop dances and celebrating catastrophic box office negotiations—is comedic perfection.
6. IT Chapter Two (2019)
The Role: The grown-up stand-up comic member of the Losers' Club who masks childhood trauma and unrequited love behind frantic wisecracks.
Stepping into the adult version of Richie Tozier, Hader provided the critical pulse of Andy Muschietti’s horror sequel. While delivering the film’s funniest one-liners, Hader subtly layered Richie with deep grief and closeted romantic longing for Eddie Kaspbrak. When the final battle turns tragic, Hader’s raw, tearful breakdown in the Derry quarry delivered the emotional gut punch of the entire saga.
5. Documentary Now! (2015–2022)
The Role: Painstaking, frame-by-frame parodies of historic documentary masterpieces, from *Grey Gardens* to *The Thin Blue Line*.
Co-created alongside Fred Armisen and Seth Meyers, Documentary Now! is high-art parody at its most refined. Hader’s chameleonic genius shone in episodes like “Sandy Passage” (a brilliant homage to the eccentric world explored in our ranking of the 10 best Drew Barrymore movies and TV shows) and “Juan Likes Rice & Chicken.” Rather than cheap mockeries, Hader treated the source material with reverent, cinematic precision.
4. The Skeleton Twins (2014)
The Role: A struggling, suicidal gay actor in Los Angeles who reunites with his estranged, equally depressed twin sister.
Craig Johnson’s Sundance breakout revealed the full depth of Hader’s dramatic capability. Reuniting with longtime sketch partner Kristen Wiig, the duo tapped into an intimate, telepathic sibling shorthand.
Their showstopping lip-sync performance to Starship’s “Nothing’s Gonna Stop Us Now”—starting as awkward embarrassment before erupting into joy—is one of the most sublime scenes in modern independent cinema.
3. Superbad (2007)
The Role: An irresponsible, joyriding police officer who takes fake-ID-toting high schooler McLovin on a wild night across town.
Greg Mottola and Judd Apatow’s teen comedy masterpiece gave Hader his cinematic breakthrough. Paired with Seth Rogen, the two created the most hilariously incompetent, affectionate cop duo since The Blues Brothers.
From doing doughnuts in empty parking lots to shooting stop signs with service weapons, Hader’s Officer Slater balanced deadpan bureaucratic negligence with pure, childlike rebellion.
2. Saturday Night Live (2005–2013)
The Role: Legendary recurring characters—from Weekend Update city correspondent Stefon to geriatric newsman Herb Welch—and flawless impressions.
During his eight seasons at Studio 8H, Bill Hader was the gold standard of live sketch comedy. His Stefon sketches—co-written with John Mulaney, who deliberately changed cue cards seconds before airtime to make Hader break on live television—became a national phenomenon.
Alongside the groundbreaking performers profiled in our retrospective on The Second City and the SNL talent pipeline, Hader’s vocal mimicry (Al Pacino, Alan Alda, Vincent Price) cemented his status as one of the top five cast members in Saturday Night Live history.
1. Barry (2018–2023)
The Role: A traumatized Midwestern hitman who travels to Los Angeles for a contract killing and becomes consumed by the local community theater scene.
There was never any debate. Over four breathtaking seasons, Barry redefined the modern television landscape, and Hader’s performance as Barry Berkman is an all-time screen triumph.
What began as a pitch-black comedy about an assassin taking acting classes evolved into a harrowing, visually stunning meditation on PTSD, guilt, human redemption, and the toxic nature of violence. As director, Hader staged action sequences (such as Season 3’s breathtaking motorcycle highway chase) with the geometric brilliance of the Coen brothers and Michael Mann.
Winning two consecutive Primetime Emmy Awards for Outstanding Lead Actor in a Comedy Series, Hader proved that he is not just a beloved comedic performer, but one of the great cinematic auteurs of the 21st century.