Movies like How I Spent My Summer Vacation (1997)
The best movies like How I Spent My Summer Vacation (1997) are Chris Rock: Kill the Messenger (2008), Ali Wong: Single Lady (2024) and Life of the Party (2018). If How I Spent My Summer Vacation hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedRicky Gervais: SuperNature (2022)7.4/10 from 385 votes
- NewestDriver's Ed (2026)Released 2026
Chris Rock: Kill the Messenger (2008)
An HBO special edited from three performances from Chris Rock's 2008 comedy tour: London (dark suit, dark shirt), Johannesburg (black suit, white shirt) and New York (shiny jacket). Topics include the ongoing presidential campaign, the possibility of a black president, George W. Bush, gas prices, low-paid jobs, ringtones and bottled water, sex, relationships and the correct use of the n-word
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisAli Wong: Single Lady (2024)
After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLife of the Party (2018)
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. Plunging headlong into the campus experience, the increasingly outspoken Deanna – now Dee Rock – embraces freedom, fun, and frat boys on her own terms, finding her true self in a senior year no one ever expected.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMuch Ado About Nothing (2013)
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Wedding Year (2019)
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.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisDriver's Ed (2026)
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisAdventures in Public School (2018)
A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThree O'Clock High (1987)
Nerdy high schooler Jerry Mitchell is assigned to write an article for the school paper about the infamous new delinquent transfer student, Buddy Revell. When Jerry accidentally invades Buddy's personal space and touches him, Buddy challenges Jerry to an afterschool fight in the parking lot, which Jerry tries to avoid at all costs.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe F**k-It List (2020)
After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJerry Seinfeld: 23 Hours to Kill (2020)
Jerry Seinfeld takes the stage in New York and tackles talking vs. texting, bad buffets vs. so-called "great" restaurants and the magic of Pop Tarts.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe After Party (2018)
When an aspiring rapper goes viral for the wrong reasons, he thinks his career is sunk. But a wild party gives him one more chance to make it right.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAziz Ansari: Nightclub Comedian (2022)
After another year of lockdowns, Aziz takes the stage to skewer pandemic life, quarantines, vaccine cards, celebrity side-gigs, smartphones and more.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThunderstruck (2012)
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.
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 thisAfter the Ball (2015)
After the Ball, a retail fairy tale set in the world of fashion. Kate's dream is to design for couturier houses. Although she is a bright new talent, Kate can't get a job. No one trusts the daughter of Lee Kassell, a retail guru who markets clothes "inspired" by the very designers Kate wants to work for. Who wants a spy among the sequins and stilettos? Reluctantly, Kate joins the family business where she must navigate around her duplicitous stepmother and two wicked stepsisters. But with the help of a prince of a guy in the shoe department her godmother's vintage clothes and a shocking switch of identities, Kate exposes the evil trio, saves her father's company -- and proves that everyone can wear a fabulous dress.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisClass Rank (2017)
Two high school misfits join forces in an attempt to overtake the local school board. Guided by their families, they enter the perilous word of politics and, in the process, learn a thing or two about love.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisChris Rock: Selective Outrage (2023)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRichard Pryor: Live in Concert (1979)
Richard Pryor delivers monologues on race, sex, family and his favorite target—himself, live at the Terrace Theatre in Long Beach, California.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisRicky Gervais: Armageddon (2023)
Ricky Gervais dishes out controversial takes on political correctness and oversensitivity in a taboo-busting comedy special about the end of humanity.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like How I Spent My Summer Vacation?
The closest matches to How I Spent My Summer Vacation are Chris Rock: Kill the Messenger (2008), Ali Wong: Single Lady (2024) and Life of the Party (2018). Below are 17 more, each with the reason it matches.
What should I watch after How I Spent My Summer Vacation?
Start with Chris Rock: Kill the Messenger (2008), the closest match to How I Spent My Summer Vacation.
What is the highest-rated movie like How I Spent My Summer Vacation?
Ricky Gervais: SuperNature (2022), rated 7.4/10 by 385 TMDB users.
What is the newest movie like How I Spent My Summer Vacation?
Driver's Ed (2026) is the most recent release on this list.
Are there English movies like How I Spent My Summer Vacation?
Yes: Chris Rock: Kill the Messenger (2008), Ali Wong: Single Lady (2024) and Life of the Party (2018).
How are movies similar to How I Spent My Summer Vacation chosen?
First come films that Trakt’s viewers watch alongside How I Spent My Summer Vacation, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.