Movies Like Steven Wright: When the Leaves Blow Away

If you liked Steven Wright: When the Leaves Blow Away (2006), a comedy movie directed by Michael Drumm, 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
Amy Schumer: Mostly Sex Stuff (2012)
★ 5.9/10Also comedy
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…
2
Gabriel Iglesias: Hot and Fluffy (2007)
★ 7.6/10Also comedy
Gabriel Iglesias is one of the fastest-rising comics today! With his unique brand of humor, lovable stage presence and wide range of voices and impressions, it's no wonder that he already has a huge fan following. Now…
3
Kevin Hart: Laugh at My Pain (2011)
★ 7.1/10Also comedy
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.
4
Dave Chappelle: The Age of Spin (2017)
★ 7.6/10Also comedy
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.
5
Jim Jefferies: Freedumb (2016)
★ 7.2/10Also comedy
Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
6
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
7
Ricky Gervais: Out of England 2 (2010)
★ 7.3/10Also comedy
The comic performs at the Chicago Theatre.
8
Gabriel Iglesias: Aloha Fluffy (2013)
★ 7.1/10Also comedy
ALOHAAAAA! Internationally acclaimed comedian, Gabriel Iglesias, returns to Comedy Central with his latest stand-up special taped at Honolulu’s Hawaii Theatre Center. Watch as Fluffy brings the house down yet again in…
9
Jen Kirkman: I'm Gonna Die Alone (And I Feel Fine) (2015)
★ 6.8/10Also comedy
Jen Kirkman's Netflix produced stand-up special as performed at the North Door in Austin, Texas.
10
Louis C.K.: Live at The Comedy Store (2015)
★ 7.3/10Also comedy
This material was developed and prepared over the last year or so, mostly in comedy clubs. This special kind of goes back to when he used to just make noises and be funny for no particular reason. It felt right to him…
11
Jerry Seinfeld: I'm Telling You for the Last Time (1998)
★ 7.4/10Also comedy
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…
12
Taking Care of Business (1990)
★ 6.3/10Also comedy
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
13
The Mouse That Roared (1959)
★ 6.4/10Also comedy
The Duchy of Grand Fenwick decides that the only way to get out of their economic woes is to declare war on the United States, lose and accept foreign aid. They send an invasion force (in chain mail, armed with bows…
14
Louis C.K.: Hilarious (2010)
★ 7.8/10Also comedy
In this unique and dynamic live concert experience, Louis C.K.'s exploration of life after 40 destroys politically correct images of modern life with thoughts we have all had...but would rarely admit to.
15
The Ladies Man (1961)
★ 6.3/10Also comedy
After his girl leaves him for someone else, Herbert gets really depressed and starts searching for a job. He finally finds one in a big house which is inhabited by many, many women. Can he live in the same home with…
16
Iliza Shlesinger: Unveiled (2019)
★ 6.2/10Also comedy
Comedian Iliza Shlesinger dissects her recent wedding with riffs on screeching bachelorette parties, that creepy garter removal tradition and more.
17
Kevin Hart: I'm a Grown Little Man (2009)
★ 7.3/10Also comedy
Fresh off the heels of appearing in movies like Superhero Movie and The 40 Year-Old Virgin, fast-talking comedian Kevin Hart stars in this live stand-up performance where he makes fun of everything and everybody…
18
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
19
Room Service (1938)
★ 6.5/10Also comedy
Broke Gordon Miller tries to land a backer for his new play while he has to deal with with the hotel manager trying to evict him and his cast.
20
Comedy Central Roast of Justin Bieber (2015)
★ 6.8/10Also comedy
Several roasters, and the master himself Kevin Hart, make fun of Justin Bieber.