Movies Like Brett Goldstein: The Second Best Night of Your Life

If you liked Brett Goldstein: The Second Best Night of Your Life (2025), a comedy and tv movie movie directed by Jeff Tomsic, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy and tv movie
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
2
John Mulaney: Kid Gorgeous at Radio City (2018)
★ 7.9/10Also comedy and tv movie
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
3
Dave Chappelle: Sticks & Stones (2019)
★ 7.5/10Also comedy and tv movie
Dave Chappelle takes on gun culture, the opioid crisis and the tidal wave of celebrity scandals in this defiant stand-up special.
4
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy and tv movie
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
5
Dave Chappelle: The Closer (2021)
★ 7.2/10Also comedy and tv movie
As he closes out his slate of comedy specials, Dave takes the stage to try and set the record straight — and get a few things off his chest.
6
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy and tv movie
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
7
Adam Sandler: Love You (2024)
★ 6.3/10Also comedy
Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.
8
Dave Chappelle: Killin' Them Softly (2000)
★ 8.1/10Also comedy and tv movie
Dave Chappelle returns for a stand-up to D.C. and riffs on politics, police, race relations, drugs, Sesame Street and more.
9
Dave Chappelle: The Dreamer (2023)
★ 6.9/10Also comedy
From his onstage tackle to the slap heard round the world, Dave Chappelle lets loose in this freewheeling and unfiltered stand-up comedy special.
10
Ricky Gervais: Humanity (2018)
★ 7.6/10Also comedy
In his first special in seven years, Ricky Gervais slings his trademark snark at celebrity, mortality and a society that takes everything personally.
11
Taylor Tomlinson: Look at You (2022)
★ 7.2/10Also comedy and tv movie
Breakups. Therapy. Bangs. Taylor's gone through some stuff since her quarter-life crisis, and she spins her mental health journey into insightful comedy.
12
Mike Birbiglia: Thank God for Jokes (2017)
★ 7.3/10Also comedy and tv movie
Mike Birbiglia declares that a joke should never end with "I’m joking." In his all-new comedy, Birbiglia tiptoes hilariously through the minefield that is modern-day joke-telling. Join Mike as he learns that the same…
13
Taylor Tomlinson: Have It All (2024)
★ 6.8/10Also comedy and tv movie
Can Taylor Tomlinson have it all? From dating woes to dream jobs to inventive dirty talk, she shares life's ups and downs in this stand-up comedy special.
14
Dylan Moran: Like, Totally (2006)
★ 7.7/10Also comedy
Dylan Moran returns with an all-new stand-up show. Unpredictable, startling, bizarre, elegiac, but above all brilliant and hilariously funny, Moran is a master of comedy.
15
Chris Rock: Selective Outrage (2023)
★ 6.2/10Also comedy
Chris Rock delivers an electric stand-up set on non-racist yoga pants, spoiling his kids, the Kardashians and his thoughts on the Will Smith fiasco.
16
John Mulaney: Baby J (2023)
★ 7.1/10Also comedy and tv movie
A chaotic intervention. An action-packed stay in rehab. After a weird couple of years, John Mulaney comes out swinging in his return to the stage.
17
Bo Burnham: Words, Words, Words (2010)
★ 7.3/10Also comedy
Bo Burnham is back with a new one-man show full of his patented songs and wordplay, as well as haikus, dramatic readings, blasphemy, and so much more in his first hour-long special, shot live in his home town of Boston.
18
Norm Macdonald: Me Doing Standup (2011)
★ 7.7/10Also comedy
Norm MacDonald, the iconic anchor of SNL's "Weekend Update" and star of the cult classic Dirty Work, is back with a vengeance.
19
Jimmy Carr: Natural Born Killer (2024)
★ 6.4/10Also comedy
Jimmy Carr refutes the idea that you can't joke about anything these days with his edgy takes on gun control, religion, cancel culture and consent.
20
Ricky Gervais: Armageddon (2023)
★ 7.1/10Also comedy
Ricky Gervais dishes out controversial takes on political correctness and oversensitivity in a taboo-busting comedy special about the end of humanity.