Movies like Milo Edwards: Sentimental (2026)
The best movies like Milo Edwards: Sentimental (2026) are Kevin Hart: Laugh at My Pain (2011), Amy Schumer: Mostly Sex Stuff (2012) and Adam Sandler: Love You (2024). If Milo Edwards: Sentimental hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedJohn Mulaney: Kid Gorgeous at Radio City (2018)7.9/10 from 259 votes
- NewestSommore: Chandelier Fly (2026)Released 2026
Kevin Hart: Laugh at My Pain (2011)
Experience the show that quickly became a national phenomenon. Get an up-close and personal look at Kevin back in Philly where he began his journey to become one of the funniest comedians of all time.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisAmy Schumer: Mostly Sex Stuff (2012)
A ratings hit! Amy Schumer debuts her one-hour special in front of a live audience at the Historic Fillmore Theatre in San Francisco. Nothing is off limits as Schumer airs every hilarious, messed up detail of her dating and sex life, from encounters with unexpected body parts to hate-filled personal grooming appointments. In her matter-of-fact raunchy style, at odds with her self-described "Cabbage Patch Kid" appearance, Schumer tells stories of a boyfriend who makes dirty requests over dinner, the way she outsmarts her birth control, and a shocking ending to a seemingly innocent cab ride.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisAdam Sandler: Love You (2024)
Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisShane Gillis: Beautiful Dogs (2023)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisJohn Mulaney: Kid Gorgeous at Radio City (2018)
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisLouis C.K.: Oh My God (2013)
Filmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for writing on his acclaimed show on FX, Louie. Performed in the round in front of a live audience, he discusses such topics as the food chain, animals, divorce, strange anecdotes, broken morality, murder and mortality.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisDave Chappelle: The Closer (2021)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisDave Chappelle: The Age of Spin (2017)
Comedy icon Dave Chappelle makes his triumphant return to the screen with a pair of blistering, fresh stand-up specials. Filmed at The Palladium in Los Angeles, California, in March 2016.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisDylan Moran: Like, Totally (2006)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisEddie Murphy Raw (1987)
Eddie Murphy delights, shocks and entertains with dead-on celebrity impersonations, observations on '80s love, sex and marriage, a remembrance of Mom's hamburgers and much more.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisRicky Gervais: SuperNature (2022)
With his signature pitch-black sense of humor, Ricky Gervais takes the stage at the London Palladium in this provocative stand-up comedy special.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisRicky Gervais: Humanity (2018)
In his first special in seven years, Ricky Gervais slings his trademark snark at celebrity, mortality and a society that takes everything personally.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisAmy Schumer: Live at the Apollo (2015)
With her unique blend of honesty and unapologetic humor, Amy Schumer is one of the funniest, freshest faces in the industry today. This October, Schumer's provocative and hilariously wicked mind will be on full display as she headlines her first HBO stand-up comedy special: 'Amy Schumer: Live at the Apollo.' Directed by Chris Rock, the one-hour special features the comedian talking about her life and was taped before a live audience at New York’s iconic Apollo Theater.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisTaylor Tomlinson: Have It All (2024)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJim Gaffigan: Quality Time (2019)
Comedian Jim Gaffigan performs live at the State Theatre in Minneapolis, MN.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRicky Gervais: Mortality (2025)
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJerry Seinfeld: I'm Telling You for the Last Time (1998)
Taped for HBO in August 1998, on the final date of Jerry Seinfeld's tour appearances at New York City's Broadhurst Theater, I'm Telling You for the Last Time presents the standup comedian's so-called "final" standup, or at least his final tour with the standup material that made him famous.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisIliza Shlesinger: Confirmed Kills (2016)
The standup sensation tackle's TV's "Shark Tank," what it means to be a woman and how to deal with the lawless party goblin that lives in us all.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAdam Sandler: 100% Fresh (2018)
Adam Sandler takes his comical musical musings back out on the road, from comedy clubs to concert halls to one very unsuspecting subway station.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisDave Chappelle: Deep in the Heart of Texas (2017)
Comedy icon Dave Chappelle makes his triumphant return to the screen with a pair of blistering, fresh stand-up specials. Filmed at the Moody Theater in Austin, Texas, in April 2015.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisLenette van Dongen: Roedel (2016)
Registration of the theatreprogram by the Dutch comedian Lenette van Dongen. Armed with the complete DVD box of dogwhisperer Cesar Milan and all Martin Gaus-books, Van Dongen starts raising a young puppy. What this world needs is a calm, confident leader. It's only a matter of time before a well-trained rescuer walks by her side. Until one day the dog trainer gets sick and everything turns out differently….
Why it matches: Similar story and style · both comedy
Jeff Dunham: I'm with Cupid (2024)
If you hate Valentine’s Day, you’re REALLY going to hate this special…Watch it with someone you love! Or alone… Or with someone you hate… With a beer.
Why it matches: Similar story and style · both comedy
Ian Lara: Romantic Comedy (2022)
In his first standalone “Entre Nos” special, Ian Lara explores the lessons learned during the pandemic, including common problems of New Yorkers during travel, and offers some essential advice to avoid risky dating experiences.
Why it matches: Similar story and style · both comedy
Vladimir Bukharov: Investor (2024)
Vova Bukharov released his third solo concert "Investor".
Why it matches: Similar story and style · both comedy
Dead Air (TBA)
At the funeral of his best friend, a struggling stand-up is confronted with giving a eulogy. Even worse, he has to confront the possibility of not being funny.
Why it matches: Similar story and style · both comedy
Sommore: Chandelier Fly (2026)
Get ready for comedic royalty as the Undisputed Queen of Comedy, Sommore, returns to Detroit for her 7th special, performing up close and personal at the Garden Theatre, recorded on June 28th.
Why it matches: Similar story and style · both comedy
Tim Minchin: Back (2022)
After selling out his world tour in record breaking time and receiving rave reviews, internationally renowned, award-winning musician, comedian, actor, writer and composer, Tim Minchin is back... Filmed in front of a live audience at London's Shepherd's Bush Empire, Back is a musical comedy spectacle of 'Old Songs, New Songs, F*** You Songs', showcasing material from all corners of Minchin's eclectic repertoire. A hilarious display of his extraordinary wit, musical virtuoso, self-mockery and philosophical observations, Back is a truly unique and unmissable show.
Why it matches: Similar story and style · both comedy
Alec Baldwin: One Night Only (2017)
Alec Baldwin, one of entertainment's most iconic actors, is honored in an exclusive black tie evening full of comedic tributes, candid personal stories and a few surprises.
Why it matches: Similar story and style · both comedy
George Carlin: Life Is Worth Losing (2005)
Carlin returns to the stage in his 13th live comedy stand-up special, performed at the Beacon Theatre in New York City for HBO®. His spot-on observations on the deterioration of human behavior include Americans’ obsession with their two favorite addictions - shopping and eating; his creative idea for The All-Suicide Channel, a new reality TV network; and the glorious rebirth of the planet to its original pristine condition - once the fires and floods destroy life as we know it.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisDane Cook: Rough Around the Edges (2007)
Dane Cook's smash-hit show Rough Around The Edges is an energetic powerhouse stand-up performance recorded live in front of a packed house at Madison Square Garden.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like Milo Edwards: Sentimental?
The closest matches to Milo Edwards: Sentimental are Kevin Hart: Laugh at My Pain (2011), Amy Schumer: Mostly Sex Stuff (2012) and Adam Sandler: Love You (2024). Below are 27 more, each with the reason it matches.
What should I watch after Milo Edwards: Sentimental?
Start with Kevin Hart: Laugh at My Pain (2011), the closest match to Milo Edwards: Sentimental.
What is the highest-rated movie like Milo Edwards: Sentimental?
John Mulaney: Kid Gorgeous at Radio City (2018), rated 7.9/10 by 259 TMDB users.
What is the newest movie like Milo Edwards: Sentimental?
Sommore: Chandelier Fly (2026) is the most recent release on this list.
Are there English movies like Milo Edwards: Sentimental?
Yes: Kevin Hart: Laugh at My Pain (2011), Amy Schumer: Mostly Sex Stuff (2012) and Adam Sandler: Love You (2024).
How are movies similar to Milo Edwards: Sentimental chosen?
First come films that Trakt’s viewers watch alongside Milo Edwards: Sentimental, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.