1. One Crazy Summer (1986)

 One Crazy Summer is kind of a dumpster fire of a movie, but in that specific way that makes it a ton of fun to watch with one of those margaritas you made because you didn’t want to drive to Myrtle Beach to get one of Jimmy Buffet’s.

A very young John Cusack plays art-school hopeful, Hoops McCann. Hoops is fresh out of high school and spends the summer with his friends, George and Squid Calamari (get it?) in Nantucket, Massachusetts. Along the way, Hoops meets a young rocker chick named Cassandra (Demi Moore), and he is pretty immediately smitten. The movie is technically a romantic comedy, but I would argue that the comedy is the focus here, especially with the inclusion of a very loud Bobcat Goldthwaite screeching his way through a scene while trapped in a rubber Godzilla costume.

There is a lot to like here. You’ll find yourself laughing at this movie way more often that you laugh with it.

2. Wet Hot American Summer (2001)

Wet Hot American Summer is an indie film darling that has reached near-cult classic status. The film is a satirical comedy that expertly parodies the summer camp genre.

Set in the summer of 1981 on the last day of camp at Camp Firewood, campers and counselors are preparing to wrap up their summer with an epic talent show. The storyline is simple in this regard, but it’s only so the ensemble cast has room to shine in their individual subplots—all of which are hilariously overdramatic renditions of classic summer camp tropes. Oh, and part of a NASA satellite is threatening to crash into the camp.

The story here really is the stellar cast, which includes so many titans of contemporary comedy. I’m talking the likes of Amy Poehler, Paul Rudd, Molly Shannon, Kevin Sussman, Joe Lo Truglio, Janeane Garofalo, Ken Marino, H. Jon Benjamin, and a slew of others not to mention the charming and hilarious turns from Elizabeth Banks and Bradley Cooper. If you are a fan of parody and haven’t seen this flick, you need to address that immediately.

3. I Know What You Did Last Summer (1997)

 Once you’ve laughed your way through One Crazy Summer and Wet Hot American Summer, maybe you want to switch things up a bit. Revisiting the 1997 slasher-horror flick, I Know What You Did Last Summer, may be just the thing you need.

Julie James and her friends hit a pedestrian while driving to the beach. The crew checks on the pedestrian to find he is looking pretty, well, dead. So, they make the only reasonable choice: throw him in the ocean. I mean, these are all promising young people with bright futures ahead of them. No need to threaten their middle-class comfort by calling the police, right?

So, Julie and her friends end up being stalked and tormented (and murdered) by a mysterious man with a hook for a hand. The whole thing plays out in that glorious and specifically 1990s horror aesthetic.

Also, don’t sleep on this cast: Jennifer Love Hewitt, Freddy Prinze Jr., Johnny Galecki, Sarah Michelle Gellar, Ryan Phillipe, and Bridgette Wilson? These folks could be on the Mount Rushmore of Adults Who Played Teenagers in the 90s.

I think I need to go watch it again!

4. 500 Days of Summer (2009)

 I might be cheating a little bit here, but I just have such an affinity for this film. Not only does it star the always-charming Joseph Gordon-Levitt as Tom Hansen and Zooey Deschanel as the titular Summer Finn. It’s also another indie with a Sundance premiere.

In the grand scheme of things, 500 Days of Summer is a pretty standard romantic comedy, with only a few exceptions. First, the narrative is delivered in a non-linear fashion. I love this kind of thing. As the story jumps back and forth to different points in the Tom and Summer’s story, the viewer is presented with a complex and nuanced exploration of romantic love.

The second way this film differs from most others in the genre is that it does not end with a traditional “happily-ever-after,” as our two main characters are not together at the end, choosing instead to go their own ways.

Still, its conclusion offers closure enough, especially considering that the central thesis of the film seems to be that old cliché: for everything there is a season. It just so happens that for Tom and Summer, that season is only 500 days.

5. Summer of Soul (2021)

A third indie film on this list that saw its curtain rise at a Sundance Film Festival, Summer of Soul became something of a critical darling last year when it was released. The film racked up tons of accolades during awards season and is sporting a 99% on Rotten Tomatoes based on 215 reviews at the time of this writing.

Summer of Soul is the directorial debut of Ahmir “Questlove” Thompson—known primarily as the percussionist for the band The Roots. Different from other movies on this list, Summer of Soul is a documentary that explores the 1969 Harlem Cultural Festival—a six-day music festival often lost in music history due to its proximity to the more widely-known Woodstock.

This is the film you’ll want to watch when it’s time to learn something valuable. It’s an important and timely documentary that features incredible archival footage of live sets from performers like Gladys Knight & the Pips, Sly and the Family Stone, Nina Simone, and Stevie Wonder.

Questlove is absolutely the right guy for this. He’s a well-versed student of the full catalog of music history. His directorial prowess is on full display here, and it has me hoping he returns to the medium sooner than later.