Will and Lesli
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.
Author
Will and Lesli
Category
Podcast website
Latest episode
May 22, 2026
Where to listen?
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Episodes
Episode 37: Windows 95: Make Sure You’re Sitting Down 22.05.2026 29:25
Click here to say Hi! Here it is. The one Will has been waiting for. In this episode, JP joins Will and Lesli to discuss none-other-than- Windows 95. The start of the start. When you can explain to Lesli what Windows actually is- email her… Gapinthe90s@gmail.com Support the show
Episode 36: Cereals of the 90s: Drink the Milk 07.05.2026 50:28
Click here to say Hi! Lesli and Will have a battle in this episode. Not over cereal type… but over milk. Will yucks Lesli’s yum, but that’s ok, she stays true to herself. Warm, sandy milk or BUST. Let us know if you sat down to a spread at breakfast- or if you read the unpronounceable ingredients in the box. Support the show
Episode 35: 1-900-Telethon: They Call You 30.04.2026 26:53
Click here to say Hi! Will and Lesli discuss a spin-off of infomercials- 900 numbers and Telethons. Will explains what a telethon is and Lesli will tell you what it ISN’T! If you know what a $300 phone bill looks like, this episode is for you! Support the show
Episode 34: JP’s Answers to His 90s Favorites: Monogrammed 22.04.2026 35:39
Click here to say Hi! JP has a chance to answer the questions that Will and Lesli answered in Episode 6. All things 90s through the eyes of another Millennial- only this time they get to see how the other half lives. Support the show
Episode 33: Under Siege: Die Hard on a Ship 01.04.2026 36:18
Click here to say Hi! This week, JP joins Will and Lesli as they talk about the 90s action film- Under Siege. A movie that stars Steven Seagal as a tough-guy chef, Tommy Lee Jones and his sweet jacket, and crazy Gary Busey. And we can’t forget one of the most important characters in the movie- Miss July 1989. We spend a solid minute trying to figure out her purpose before concluding…there wasn’t...
Episode 32: Toy Story: It’s All in the Details 23.03.2026 34:55
Click here to say Hi! In this episode, Will and Lesli revisit Toy Story - the movie that made history as the first fully computer-animated film ever—and somehow still holds up ridiculously well. Along the way, they get way too excited about all the tiny details most people miss, from hidden Easter eggs to jokes that definitely hit harder as adults. Expect plenty of nostalgia, some laughs, and at l...
Episode 31: Infomercials of the 90s: With a sharp left into Adult Movie sections. 04.02.2026 34:37
Click here to say Hi! Lesli and Will discuss infomercials of the 90s. If you lived in the 90s, then you must remember waking up at 2 AM on the couch, listening to the ramblings of the Flowbee or Buns of Steel. Put on a bow tie and talk real fast, and you could have sold us anything! Somewhere along the way, Lesli and Will veer into the awkwardness that was Adult Movie sections of video stores of t...
Episode 30: What’s that Sound? 90s Edition: The Sweet Sound of Commercialism 28.01.2026 24:44
Click here to say Hi! Lesli and Will test their memory while Will plays various sounds from the 90s. Some sounds everyone will know, and some may only be known by former Latch-Key kids raised by an old box TV. And listen carefully! Maybe you’ll catch the sound of Will squealing with excitement at the sound of Windows 95. Guy’s enamored. Support the show
Episode 29: Beanie Babies: Not your kid’s college fund 14.01.2026 17:45
Click here to say Hi! Will and Lesli discuss the 90s craze - Beanie Babies. These pellet-filled little animals took the nation— and The-Rachel-Haircut-Moms by storm. They made their way through shops, McDonalds, and Divorce Proceedings. People waited on line and swallowed their pride to buy everything from Legs the Frog to the Princess Diana Bear. While Lesli and Will never fell into the hype, it...
Episode 28: Scrunchies: The Casual Cool Accessory of the 90s. 08.01.2026 21:25
Click here to say Hi! Listen as Will comes up with a great idea for an episode and then makes fun of Lesli for discussing it. Not to be confused with every other episode. Whether you used satin or velvet, or joined the Dead Heads with the Aztec-patterned drug-rug-material scrunchies, you can’t think of the 90s without thinking of this amazing hair accessory. Support the show
Episode 27: Giving Mall Food a Second Chance: Extra casing 30.12.2025 46:13
Click here to say Hi! Lesli surprises Will with some of the mall treats they talked about in the last episode. Some held up, some did not. But one thing’s for sure, you MUST remove the casing before you gnaw into a Summer Sausage. That- and- peach rings 4eva! Support the show
Episode 26: The Mall in the 90s: The Cool Place to Hang 04.12.2025 55:22
Click here to say Hi! The Generation Gap is big in this one. Lesli LIVED for the mall, while Will could take it or leave it. We’ll leave it to the listeners to decide which co-host they would have wanted to hang at the mall with. No matter who is chosen though, you’d be sure to enjoy sour patch kids, Auntie Ann’s Pretzels, acting stupid, and maybe a cassingle or two. Support the show
Episode 25: This or That: 90s Edition 19.11.2025 43:59
Click here to say Hi! 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? Support the show
Episode 24: Technology of the 90s: Who Picked Up the Phone? 11.11.2025 50:53
Click here to say Hi! 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. Support the show
Episode 23: Scream: Starring Drew Barrymore 22.10.2025 1:26:27
Click here to say Hi! 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 lev...
Episode 22: Hocus Pocus: A 90s Halloween Classic 15.10.2025 1:29:02
Click here to say Hi! 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 di...
Episode 21: Halloween in the 90s: Costumes, Candy, and Movies 08.10.2025 52:06
Click here to say Hi! 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. Support the show
Episode 20: Misheard Lyrics of the 90s: Isn’t that what they said? 01.10.2025 33:27
Click here to say Hi! 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. Support the show
Episode 19: Three Generations of High School: The Good, the Bad, the Bathroom dilemma 25.09.2025 1:06:47
Click here to say Hi! 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. Support the show
Episode 18: The OJ Simpson Story: If the Glove Don’t Fit 13.09.2025 45:15
Click here to say Hi! 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. Support the show
Episode 17: Amy Fisher and Joey Buttafuoco: 28.08.2025 21:19
Click here to say Hi! 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. Support the show
Episode 16: Y2K: Doomsday or just another day? 20.08.2025 26:27
Click here to say Hi! 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 th...
Episode 15: Diggstown: A 90s movie with genre confusion 13.08.2025 49:45
Click here to say Hi! 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 agre...
Episode 14: The Bobbit Case: Got a Big Gulp? 05.08.2025 21:38
Click here to say Hi! 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… Support the show
Episode 13: Heaven’s Gate: just give me the applesauce 29.07.2025 29:52
Click here to say Hi! 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. Support the show
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