Malcolm in the Middle — “Traffic Jam” (Season 2, Episode 1)
One of the things that set Malcolm in the Middle apart from its many family-sitcom contemporaries was the way that it gleefully subverted the popular tropes associated with the genre. “Traffic Jam” is a technically the second half of an unofficial two-part episode. The first part is the actual “vacation” to a water park with Malcolm and Reese (Dewey’s hysterical road trip by his lonesome is a great b-plot), and the second is the drive home. When the family gets caught in a traffic jam, they all end up in their own self-contained stories: Hal grapples with mortality, Lois can’t deal with not being in control, Reese is obsessed with a nearby ice cream truck, and Malcolm poorly entertains a love interest. It’s a total flip on the summer vacation episode: the vacation is a traffic jam, the family is not together, and everyone generally has a shitty time — but it never stops being funny.
Daria — “Is It Fall Yet?”
Daria, arguably the best scripted show that has ever existed on MTV, aired two made-for-television movies. “Is It Fall Yet?” took place between the fourth and fifth seasons, and went deep into the new relationship between Daria and Tom and the fractured friendship between Daria and Jane. It’s a summer vacation movie for misanthropes — Daria’s vacation is rife with emotional discomfort, Jane has fled to art camp where she temporarily questions her sexuality — but that just means it fits perfectly within the show’s tone.
Roseanne — “We’re Going To Walt Disney World” and “Disney World War II” (Season 8, Episodes 17-18)
For a while, it seemed every family on television took a trip to Disney World. This was obviously doubly so for ABC sitcoms. Running off to Disney doesn’t fit with Roseanne‘s tone (or financial status; this occurred before the lottery season), and the story goes that Roseanne Barr didn’t want to do this two-parter but was forced to by the network. But the episodes are great and funny (and the trip is when Darlene gets pregnant!), and it was refreshing to see a little cynicism directed at the happiest place on Earth. More importantly, though, the episode served as a perfect segue into the following episode, “Springtime for David,” which lampooned Disney World. David goes to work for an amusement park that’s eerily similar to Disney, and the entire episode basically just pokes fun at the too-cheery atmosphere of the park.
Mad Men — “The Jet Set” (Season 2, Episode 11)
Mad Men doesn’t exactly have a light, summery vibe, which is perhaps why I like its vacation-y episodes so much. In Season 2’s “The Jet Set,” Don Draper somewhat enjoys a quick business trip/vacation to Los Angeles. There’s a great moment where he stands poolside, still in his suit coat and hat, smoking a cigarette amongst people in swimsuits after the airline lost his luggage. From there, Don suffers from heat exhaustion and collapses at a party, but, in true Don Draper fashion, still manages to sleep with the beautiful stranger from a bar. Don and Joy have a fun summer fling, but, as always, there’s something darker lurking beneath the surface.
Salute Your Shorts — The Entire Series
OK, so I’m cheating a bit with this one, but watching the whole series — only two seasons — is totally worth it. The entire show is a summer vacation, taking place at a sleep-away camp (Camp Anawanna!) and focused on a group of teenagers and their counselors. It featured funny and familiar situations for children who attend camp every summer and provided an intriguing look into a world that us kids who didn’t get to go were thoroughly jealous of. It’s impossible to pick just one episode that fully encapsulates that summer vacation feel — though it’s worth mentioning that Zeke the Plumber still terrifies me to this day.
Degrassi — “Paradise City” (Season 8, Episodes 19-22)
“Paradise City” is also known as “Degrassi Goes Hollywood,” and was marketed as a made-for-television movie before being separated into four different episodes for syndication purposes. Wherever you stand on the issue of Degrassi — it is both overrated (by its fans) and underrated (by critics) — it’s easy to find yourself enjoying its ridiculous campiness. “Degrassi Goes Hollywood” marked the separation between old-school and new-school fans — it was Paige’s last official episode and the last real arc for Manny before she fled the next season. Taking place during spring break (which is basically just summer in Canada, right?), the a-plot is predictably light and silly (the girls are in Hollywood trying to become famous actresses); the b-plot is surprisingly dark, centering around Ellie’s father’s PTSD from Afghanistan and Ellie’s depression. The episode juxtaposes the ridiculousness of Hollywood with Ellie’s suicide attempt, but, as expected, has a happy ending.
The Simpsons — “Summer of 4 Ft. 2” (Season 7, Episode 25)
You can’t talk about vacation episodes without talking about The Simpsons. They’ve gone everywhere — New York City, Australia, Tokyo — but I’ve always loved the simplicity of “Summer of 4 Ft. 2” where the family (and Milhouse) goes to Ned’s beach house. Lisa seizes the opportunity to reinvent herself, shedding her nerdy qualities and befriending some skateboarders (the pinnacle of coolness). It’s a wonderful and sweet Lisa episode — even Bart, who originally sells her out, does something nice at the end — especially when it ends with her friends accepting Lisa as is.