Aside from stretching your legs, finally reconnecting with running water and not sitting next to your siblings/friends/pets for one goddamn minute longer, the best thing about wrapping up a road trip is turning on the TV at your destination and revisiting classic fictional versions of what you just endured.
Like all great road-trip movies, this is less about the destination (a 10-year high school reunion in Tucson, Arizona, where BFFs Romy and Michele must confront the bullies, crushes and memories they moved far away from after graduation) than it is the journey that gets them there. Filled with flashbacks and attempts at new identities, this ’90s flick is like a fine wine: it only gets better with age.
There’s nothing at the end of this wild ride for Thelma, a mistreated housewife, and her best friend, Louise, a waitress, except freedom from the systems and people that keep them down. With guns on their hips, Brad Pitt in their backseat and the Grand Canyon on the horizon, they strap in and hold each other’s hands through shoot-outs and high-speed chases right until the end.
Nothing says ’90s nostalgia like a made-for-TV movie starring Jonathan Taylor Thomas. In I’ll Be Home for Christmas, the heartthrob plays Jake, a cocky college kid whose nemesis pranks him and leaves him stranded in the desert in a Santa suit. He’s got to make it across the country in time to get his girl (Jessica Biel, pre-JT) and the vintage car his dad is gifting him. Cue: antics!
“The most time-honoured tradition of them all: the road trip.” Torn between his long-term, long-distance relationship and a potential love affair right in front of him, university student Josh gathers his buffet of bros and embarks on a raucous cross-country trip to catch the sex tape he mistakenly posted to his girlfriend – before she sees it.
Britney Spears returned to her Mickey Mouse Club roots when she went from pop star to leading lady in this turn-of-the-millennium movie about childhood friends reconnecting after high school. In a convertible driven by a potential felon, Lucy (Spears), Kit (Zoe Saldana) and Mimi (Taryn Manning) are on a journey to find Lucy’s mother, taking pitstops for karaoke and D&Ms along the way.