Generation Gap in the 90s

Generation Gap in the 90s

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

November 19, 2025 43 mins

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Will and Lesli have to choose This or That between 90s items. Some are a little rough… Forrest Gump running or Jack and Rose swimming? And some are no brainers.. like Home Alone over Mrs. Doubtfire. But who knew that Mariah Carey could almost end a friendship?  See what you think. Do you agree with their choices?

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Lesli and Will discuss technology of the 90s with their guest Eric. Lesli will never give up trying to play Frogger or Q-Bert, but she does give up trying to explain to the boys how a Brother Word Processor works. I guess you had to be there.

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Will and Lesli are joined by Gen X’ers Melissa and Eric to discuss the 90s horror flick Scream. Like every other sucker, they were lured in by the promise of Drew Barrymore, only to find she lasted as long as her dark, matte lipstick - not very long. We’re still not sure which loss was more devastating to Lesli, but it probably rhymes with dipstick. 

So if Scream was your level of scary, and you love a good disc...

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Lesli and Will have a guest join them in discussing the 90s Halloween cult classic- Hocus Pocus. Christine is a super fan! Of the movie- not our show. She’s never listened to an episode. But you wouldn’t know it, because she jumps right in and doesn’t miss a beat. And her sidekick Pam joins to add to the laughs. So lace up your cross-trainers and join them as they run amok discussing every detail and every bad ...

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It’s getting crispy out! And we know what that means. Halloween is coming and Lesli and Will are psyched to discuss it! We can help Will overcome some costume trauma,  and we can convince Lesli that the baby-sized fun candy bars aren’t a personal attack on her! And make sure to send Will a shout-out about his spooky voice. He was really excited about it.

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Will and Lesli discuss the misheard lyrics of the 90s. There wasn’t easy access to lyrics back then, so you sang what you heard. And sometimes…. You misheard! Linger…Spoiler: she wasn’t looking for food. 

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Once again, Will and Lesli have 3 generations on Generation Gap in the 90s. Lesli’s daughter Teagan is back, and this time she brought a friend- Rachael. They discuss what’s the same in high school, what’s different, and they realize that Gen Z thinks a phone is synonymous with a camera. 

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Lesli and Will discuss one of the biggest stories of the 90s. So big it made it into the intro of Generation Gap in the 90s. They discuss OJ Simpson and the murder of his ex-wife Nicole Brown, and her friend Ron Goldman, along with the trial watched around the world.

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Will and Lesli discuss one of the biggest tabloid stories of the 90s: Amy Fisher and Joey Buttafuoco. An autobody shop owner from Long Island has an affair with a 16 year old girl which results in a near-deadly attack on his wife. Although, if you ask Will and Lesli, there was more than one victim in this situation. 

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Y2K. The Millennium. Doomsday. Whether you were a prepper or a partier, every Gen X and Millennial remembers where they were on December 31, 1999. Whether you were expecting planes to fall from the sky or you were expecting another round of drinks when the clocks hit midnight, the switch from 1999 to 2000 was one to remember. Will and Lesli discuss where they were and what they were doing on that night. Spoiler...

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Lesli and Will discuss the 90s movie Diggstown, starring James Woods, Louis Gossett Jr, and Oliver Platt. 

Lesli’s husband said it was underrated in the 90s. Lesli and Will had to watch it to find out why. It’s boxing, it’s con-artist, and it’s small-town- which may or may not be a genre. 

Either way, there’s definite genre confusion. Gapinthe90s@gmail.com to tell if you agree or disagree.

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Lesli and Will discuss the insane case of Lorena Bobbit and how she chopped off her husband’s…. Bobbit. Temporary insanity? He deserved it? You decide…

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Will and Lesli discuss one of the most famous cults of the 90s: Heaven’s Gate. Did they get to choose a flavor? A bunk? A sneaker? Listen and find out.

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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?

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July 7, 2025 59 mins

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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 of the 90s will force you to have str...

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June 11, 2025 62 mins

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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.

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June 4, 2025 56 mins

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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! 

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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.

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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. 


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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 boombox like the bad-ass he is. Did we men...

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