Movies Like Not Cool

If you liked Not Cool (2014), a comedy and romance movie directed by Shane Dawson, 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
The Big Picture (1989)
★ 5.9/10Also comedy and romance
Hollywood beckons for recent film school grad Nick Chapman, who is out to capitalize on the momentum from his national award-winning student film. Studio executive Allen Habel seduces Nick with a dream deal to make his…
2
St. Elmo's Fire (1985)
★ 6.1/10Also drama and romance
Reluctant to let go of college life, a close-knit team of seven friends--irresponsible saxophone player Billy, young Republican Alec, his girlfriend Leslie, struggling journalist Kevin, drama queen Jules, lovesick…
3
Cyrus (2010)
★ 5.9/10Also comedy and drama
With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before…
4
Seven Minutes in Heaven (1986)
★ 6.1/10Also comedy and drama
Natalie allows her classmate Jeff, who has run away from home, to stay at her place while her father is away on a business trip. Natalie soon starts dating Jeff's friend James Casey, who isn't as faithful as she…
5
The Clique (2008)
★ 5.9/10Also comedy and drama
A young girl tries to fit in with a clique of popular middle school girls after moving into the guest house of one of their homes.
6
10 Years (2012)
★ 5.8/10Also comedy and drama
A group of friends reunite ten years after their high-school graduation.
7
ATL (2006)
★ 7/10Also drama and comedy
As four friends prepare for life after high school, different challenges bring about turning points in each of their lives. The dramas unfold and resolve at their local rollerskating rink, Cascade.
8
The Map That Leads to You (2025)
★ 6.7/10Also romance and drama
Heather is a young woman traveling Europe with friends before starting her perfectly planned life. A chance meeting with Jack sparks an unexpected romance that leads to deep emotional discovery. As secrets and life…
9
Starting Over (1979)
★ 6.4/10Also comedy and romance
After divorcing his ambitious singer wife, a middle-aged man begins a new relationship with a teacher.
10
Numb (2007)
★ 5.9/10Also comedy and drama
Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink, but nothing works. The Golf Channel…
11
XX/XY (2002)
★ 6/10Also drama and comedy
Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.
12
Delirious (2007)
★ 6.3/10Also comedy and drama
Les, a small-time celebrity photographer desperate to make it big, befriends Toby, a homeless young man with no direction except a vague desire to become an actor. When by chance, Toby becomes romantically involved…
13
No Hard Feelings (2023)
★ 6.7/10Also comedy and romance
On the brink of losing her childhood home, Maddie discovers an intriguing job listing: wealthy helicopter parents looking for someone to “date” their introverted 19-year-old son, Percy, before he leaves for college. To…
14
Beautiful Girls (1996)
★ 6.7/10Also comedy and drama
During a snowy winter in the small fictional town of Knight's Ridge, Massachusetts, a group of lifelong buddies hang out, drink and struggle to connect with the women who affect their decisions, dreams and desires.
15
House of D (2004)
★ 6.3/10Also comedy and drama
In the present, artist Tom Warshaw recalls his traumatic coming of age. As a 13-year-old growing up in New York City in 1973, Tom hangs out with Pappass, a mentally disabled man. With Tom's mother battling depression…
16
Sitting in Bars with Cake (2023)
★ 7/10Also romance and comedy
Extrovert Corinne convinces Jane, a shy, talented baker, to commit to a year of bringing cakes to bars, to help her meet people and build confidence. But when Corinne receives a life-altering diagnosis, the pair faces…
17
Why Did I Get Married Again? (2026)
★ 6.7/10Also comedy and romance
The couples reunite for the destination wedding of Marcus and Angela's daughter, bringing drama old and new as they ask, "Why did we get married again?"
18
The Best You Can (2025)
★ 7/10Also comedy and romance
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside…
19
Madame (2017)
★ 5.9/10Also romance and comedy
Anne and Bob, a well-to-do American couple, have just moved to a beautiful manor house in romantic Paris. To impress their sophisticated friends, they decide to host a lavish dinner party, but must disguise their maid…
20
Love & Sex (2000)
★ 6.2/10Also comedy and drama
When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back…