Movies Like The Smart Way

If you liked The Smart Way (1937), a comedy movie directed by William Watson, 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
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.
2
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…
3
Chris Rock: Bring the Pain (1996)
★ 7.2/10Also comedy
A true equal-opportunity offender, Chris Rock's brand of humor will make you think after you're done laughing.
4
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
5
The Wedding Year (2019)
★ 5.9/10Also comedy
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
6
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.
7
Thunderstruck (2012)
★ 6.2/10Also comedy
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
8
Chris Rock: Never Scared (2004)
★ 7.5/10Also comedy
Chris Rock, the three-time Emmy Award-winner, comedian, actor, and host of HBO's acclaimed The Chris Show, stars in his fourth solo stand-up special for HBO, Chris Rock: Never Scared. Featuring his unique, insightful…
9
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedy
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
10
Aziz Ansari: Live at Madison Square Garden (2015)
★ 6.5/10Also comedy
Ansari headlines the iconic Madison Square Garden and delivers his most hilarious and insightful stand-up yet. Filmed in front of a sold-out audience, Ansari's latest special is an uproarious document of the comic in…
11
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7.1/10Also comedy
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
12
Eddie Izzard: Circle (2002)
★ 7.6/10Also comedy
Town Hall, New York City, 26 June 2000. An evening with Eddie Izzard in which she moves back and forth in time, with religion as the loose but constant theme.
13
Cadet Kelly (2002)
★ 6.2/10Also comedy
Hyperactive teenager Kelly is enrolled into a military school when her new stepfather becomes the Commandant. At first she has problems fitting in and taking orders until she tries out for the drill team.
14
Richard Pryor: Live in Concert (1979)
★ 7.4/10Also comedy
Richard Pryor delivers monologues on race, sex, family and his favorite target—himself, live at the Terrace Theatre in Long Beach, California.
15
Eddie Izzard: Definite Article (1996)
★ 7.8/10Also comedy
Eddie arrives on stage through a huge book which opens to reveal herself sitting at the top of a staircase. Then discusses Caesar dog food, 24 hour garages, Latin, and winds her way through James Bond gadgets, Einstein…
16
Life of the Party (2018)
★ 6.1/10Also comedy
When her husband suddenly dumps her, longtime dedicated housewife Deanna turns regret into re-set by going back to college... landing in the same class and school as her daughter, who's not entirely sold on the idea…
17
Duplex (2003)
★ 6.1/10Also comedy
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
18
Hannibal Buress: Animal Furnace (2012)
★ 7.1/10Also comedy
Hannibal is a Chicago native, currently living in New York City where he regularly performs and lives alone with no pets. Animal Furnace was recorded in December of 2011. Hannibal's credits include writing for 30 Rock…
19
Aziz Ansari: Intimate Moments for a Sensual Evening (2010)
★ 6.8/10Also comedy
Aziz Ansari presents his highly anticipated debut hour long stand-up special. The critically acclaimed stand-up and actor (Parks and Recreation, Funny People) discusses topics ranging from sheets with fraudulent thread…
20
Demetri Martin: The Overthinker (2018)
★ 6.8/10Also comedy
With his signature one-liners and drawings, Demetri Martin muses on doughnut holes, dogs, sports bars, the alphabet's most aggressive letters and more.