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Generation Gap in the 90s

Will and Lesli
3 episodes   Last Updated: Apr 23, 25

The podcast where a Gen X girl and a Millennial guy dive deep into the decade that defined us. From OJ to Y2K, VHS tapes to the dawn of the DVD, we're revisiting movies, music, and events that shaped a generation - or in our case, two generations.

Episodes

Click here to text us and say hi. You might even get a shout out on a future episode.On Generation Gap in the 90s, we’re rewinding to Ace Ventura — where we swap memories of the quirky and quotable pet detective as he solves the case of the missing Miami Dolphins mascot, Snowflake. Allll righty, then! Tell us your favorite part at gapinthe90s@gmail.com! We’d love to do some shout-outs on our next episode!Support the show
Click here to text us and say hi. You might even get a shout out on a future episode.Snacks from the 90s were basically edible happiness wrapped in neon packaging and questionable nutrition. Gen X kids ate them at a stop at their locker or in their concrete-walled dorms. Meanwhile, millennials proudly flaunted their plastic lunch boxes like they were carrying solid gold. If your mom packed you just the right snack , you were basically cafeteria royalty. It wasn’t just lunch—it was snack-based social currency, and if you didn’t guard your snacks, someone would trade you a carrot stick for your high fructose-filled, red#5 snack and call it “a good deal.”Support the show
Click here to text us and say hi. You might even get a shout out on a future episode.From nudie magazine day to academic decathlon meltdowns, Billy Madison is more than just a silly comedy—it's a cultural touchstone that defined humor for an entire generation.In this nostalgia-packed episode, we unpack what makes Adam Sandler's 1995 breakthrough film still resonate with audiences nearly three decades later. Our Gen X host Lesli reflects on experiencing the movie in college, while millennials Will and JT share how discovering it as kids in the 90s shaped their sense of humor forever.We dive deep into the film's most quotable moments—from "O'Doyle rules" to "You blew it" to the infamous "I award you no points" speech—and explore how these lines have seamlessly integrated into our collective vocabulary. The conversation reveals fascinating insights about how differently generations experienced this comedy classic, with scenes that hit differently depending on whether you were 11 or 19 when you first watched.Beyond the laughs, we examine what made Billy Madison the perfect launchpad for Sandler's unique comedy style, how it showcased future stars like Norm MacDonald and Chris Farley, and why its silly, no-apologies approach to humor feels strangely timeless even when parts haven't aged perfectly.Whether you're revisiting this film for the hundredth time or curious about why people still reference a movie about a grown man repeating elementary school, this episode offers a hilarious, thoughtful exploration of Billy Madison's enduring legacy. So grab your snack pack, avoid any banana peels on the ground, and join us for this celebration of 90s comedy at its most quotable.Support the show