Movies Like Surfing the Web

If you liked Surfing the Web (2019), a comedy movie directed by Nicholas M. Garofolo, 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
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.
2
And Now for Something Completely Different (1971)
★ 7.2/10Also comedy
A collection of Monty Python's Flying Circus skits from the first two seasons of their British TV series.
3
Monty Python Live at the Hollywood Bowl (1982)
★ 7.4/10Also comedy
Monty Python perform many of their greatest sketches at the Hollywood Bowl, including several from pre-Python days.
4
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.
5
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…
6
The Cheap Detective (1978)
★ 6.4/10Also comedy
A spoof of the entire 1940s detective genre. San Francisco private detective, Lou Pekinpaugh is accused of murdering his partner at the instigation of his mistress—his partner's wife.
7
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…
8
Family Guy Presents: Blue Harvest (2007)
★ 7.4/10Also comedy
With the Griffins stuck at home during a blackout, Peter tells the story of "Star Wars Episode IV: A New Hope".
9
Caveman (1981)
★ 6.7/10Also comedy
Disgraced and cast out of his tribe for lusting after Lana, the mate of the tribe's head muscle man, Atouk stumbles along gathering other misfits and learning a bit about the world outside of his cave. Eventually he…
10
Ricky Gervais: Out of England 2 (2010)
★ 7.3/10Also comedy
The comic performs at the Chicago Theatre.
11
American Dreamer (2022)
★ 6/10Also comedy
In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
12
Dog Gone (2008)
★ 6.5/10Also comedy
A courageous boy battles a gang of bumbling thieves to rescue a dog carrying a fortune in stolen diamonds.
13
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…
14
Dave Chappelle: The Bird Revelation (2017)
★ 7.5/10Also comedy
Comedy juggernaut Dave Chappelle's fourth Netflix Special, taped on November 20th, 2017 at Los Angeles' Comedy Store.
15
Go West (1940)
★ 6.6/10Also comedy
A con man heading west to search for gold teams up with a pair of scheming brothers along the way. The trio soon find themselves in the middle of a feud between two rival families and two underhanded land developers.
16
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.
17
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…
18
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…
19
Airplane II: The Sequel (1982)
★ 6.1/10Also comedy
A faulty computer causes a passenger space shuttle to head straight for the sun, and man-with-a-past Ted Striker must save the day and get the shuttle back on track – again – all the while trying to patch up his…
20
Rowan Atkinson Live (1992)
★ 8.2/10Also comedy
Rowan Atkinson and Angus Deayton in Boston doing a live performance of the same styles of humor we've seen in Mr. Bean and Blackadder. Included are lessons on Shakespearean acting, a school headmaster meeting with the…