Will and Lesli

Generation Gap in the 90s

Tv EN ↓ 37 episodes

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.

Author

Will and Lesli

Category

Tv

Latest episode

May 22, 2026

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Episodes

Episode 12: The Summer of 1994: Summer memories of the 90s as a 10-year old and an 18 year old 22.07.2025

Click here to say Hi! The Summer of 1994. Whether you were 10 like Millennial Will or 18 like Gen X Lesli, the Summer of 94 was a summer to remember. The days were slower, the music was great, and all was right with the world. What do you remember about the Summer of 1994? Support the show

Episode 11: Sitcom Smackdown 08.07.2025

Click here to say Hi! Will and Lesli put 90s character against 90s character in the ring and discuss who would get their ass kicked. Will it be strength? Will it be sass? Will it be pent up anger? What will it be that determines the winner? Will Joey fight Carlton? Will the Fresh Prince fight Al Bundy? And who will end up the Ultimate Winner?  Whether you’re a Gen X or a Millennial, your memories...

Episode 10: Board Games of the 90s 11.06.2025

Click here to say Hi! In Episode 10: Board Games in the 90s, Will and Lesli discuss the Board Games they loved and the Board Games they didn’t.  They discuss the feelings of 90s nostalgia and the memories of having a panic attack waiting for the Operation buzzer or Perfection to go off. Were they sore losers or board flippers? Listen and find out. You may even catch a 90s jingle or two. Support th...

Episode 9: Soundtracks of the 90s 05.06.2025

Click here to say Hi! In Episode 9: Soundtracks of the 90s, Will and Lesli discuss their favorite songs made for movies, and their favorite soundtracks. If you are a Millennial or a Gen Xer who loves all things 90s like we do, you’ll love the discussion that incorporates two of our favorite things… 90s movies and 90s music!  #GenerationXMovies #GenerationXMusic Support the show

Episode 8: Lesli’s Junior Year ‘92-‘93 28.05.2025

Click here to say Hi! In this episode, Lesli and Will attempt to keep their ADHD in check while they discuss the best school year of Lesli’s life - her Junior Year. From getting her braces off to getting her license, losing stupid bets to working at Baskin Robbins - Lesli reminisces about being 17 in 1993. Support the show

Episode 7: Tommy Boy: Farley’s Physical Comedy 23.05.2025

Click here to say Hi! In this episode, Lesli and Will are joined by special guest JP to dive into the classic ‘90s comedy Tommy Boy. Together, they revisit the unforgettable Chris Farley and David Spade masterpiece.  It’s full of laughs while still holding on to some heartfelt scenes.  #GenerationXMovies Support the show

Episode 6: 90s Nostalgia Differences: Boomboxes and Bubbles 14.05.2025

Click here to say Hi! This week's episode is a hilarious stroll down memory lane as Lesli and Will compare 90s memories that scream nostalgia.  Lesli confesses to her alter ego named Bubbles with her Dorothy-Hamill-haircut and to making prank calls and throwing roses on stage at her first concert; while Will confesses to his obsession with the Casio keyboard demo song and to carrying a boombo...

Episode 5: A Gen Z’s Knowledge of 90s 07.05.2025

Click here to say Hi! Teagan, a Gen Z high school senior, bravely attempts to explain her knowledge of 90s culture to Millennial Will and Gen X Lesli. Listen as Teagan discovers the seriousness of pogs and schools Will and Lesli on a couple things from the Gen Z world. Support the show

Episode 4: 90s Sitcoms: Our Top 5 Most Watched Sitcoms 30.04.2025

Click here to say Hi! Will and Lesli discuss their top 5 most-watched sitcoms of the 90s. Whether you love the sound of canned laughter or you love pointing out the over-acting, you’ll feel like a kid again- glued to the TV screen with the sound of mom cooking dinner in the background. Support the show

Episode 3: Laces Out: Remembering Ace Ventura- Pet Detective 23.04.2025

Click here to say Hi! 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! #GenerationXMovies Support the show

Episode 2: Snackin’ Like it’s 1999! 09.04.2025

Click here to say Hi! 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 wa...

Episode 1:Billy Madison: a film that gave an entire generation (or two) their favorite movie quotes. 02.04.2025

Click here to say Hi! 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 experien...

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