The TDWS Playlist

What is the most “Gen X” song of all time?

Updated July 3, 2026

It’s no secret that part of my morning routine is to pour a cup of coffee (hot, black), and sit back to watch The Daily Whatever Show, hosted by Dana DuBois and Lawrence Winnerman. The topics are always interesting, and the guests are amazing. In these uncertain times, it’s nice to have something to look forward to each day!

At the end of each show, new guests are always asked “the question.”

What is the most Gen X song of all time?

This question either temporarily paralyzes the guest, or causes an immediate reaction. There is, of course, no right or wrong answer, but some songs definitely get nominated multiple times. Since Gen X spans from roughly 1965-1980, that’s a huge range of songs to choose from. I always enjoy hearing the suggestions from people who didn’t grow up Gen X. They often have some amazing picks!

Earlier this year, I took it upon myself to start compiling the songs from each episode and putting them into a shareable playlist online. This wasn’t easy, as not every episode has a searchable transcript. Nevertheless, I persisted. I started working up a list on my computer, along with who the contributor was. Then, I set these songs up into shared playlists on Spotify and Apple Music. Show moderator Yanni Hamburger set up the list over on YouTube, if you prefer videos!

With over four hours of awesome songs, you should add it to your favorites!

I shared the playlist with our driver in Portugal, and he put it on the stereo in the van!!

Listen on Spotify

It’s also on Apple Music

The Playlist

So, here we go—the list of songs as nominated by guests of The Daily Whatever Show (as far as I have been able to compile).

• Heart of Glass | Blondie: Lawrence Winnerman

• Relax | Frankie Goes to Hollywood: Stephanie G Wilson, PhD

• Bitchin’ Camaro | Dead Milkmen: Jenn Budd

• Don’t You Forget About Me | Simple Minds: Jason Odell Andrea Hoffmann

• Smells Like Teen Spirit | Nirvana: Walter Rhein, Lorissa Rinehart, Lana Li, Michelle Kinney, Nabil Ayers

• Creep | Radiohead: Liz LaPoint

• Zombie |The Cranberries: Ahmed Baba

• Everybody Wants To Rule The World | Tears for Fears: Bob Cesca

• The Greatest Love of All | Whitney Houston: Teri Leigh 💜

• Hungry Like the Wolf | Duran Duran: Leo Caldwell

• The Reflex | Duran Duran: Zev Shalev

• Smooth | Santana: Anne P. Mitchell, Esq.

• Livin’ on A Prayer | Bon Jovi: Qasim Rashid, Esq., Letters from a Feminist, Katrina Anne Willis

• The Answer | Bad Religion: Ellie Leonard

• Heaven | Bryan Adams: Kait Justice

• Girls Just Wanna Have Fun | Cyndi Lauper: Amie Simon, Mona Das

• Pump it Up | Elvis Costello: Zuri Stevens

• Night Swimming | REM Melissa Corrigan, she/her

• Tainted Love | Soft Cell: Dana DuBois, Matt McNeil

• Ray of Light | Madonna: Polly Walker Blakemore

• Catch Me I’m Falling | Pretty Poison: Stephen Robinson

• Self Esteem | The Offspring: Stephanie Drury

• Don’t Stop Believin’ | Journey: Christian Finnegan

• We’re Not Gonna Take It | Twisted Sister: Lisa | We Are The Third Estate

• No Diggity | Blackstreet feat. Dr. Dre Dr. Amber Hull

• You Spin Me Round | Dead or Alive: Mr. Troy Ford

• If You Were Here | Thompson Twins: Julie Roginsky

• Viva La Vida | Coldplay: Shane Yirak

• Goodbye Yellow Brick Road | Elton John: Mike Nellis

• You Oughta Know | Alanis Morisette: 🧿Grey Galaxie🧿

• Dear God | XTC: NeuroDivergent Hodgepodge

• Wildfire | Michael Murphy: Char Sundust

• If You Leave | OMD: Andra Watkins

• Fuck and Run | Liz Phair: Kristi Coulter

• Suggestion | Fugazi: Christopher Pepper

• Pearl Jam | Even Flow / Let’s Go Crazy | Prince: Maritsa Georgiou

• China Grove | Doobie Brothers: Grounded with Jon Tester & Maritsa Georgiou

• I Can’t Go for That/Out of Touch | Hall & Oates: Hallie-Claire Weems

• Would | Alice in Chains: THE LEFT HOOK with Wajahat Ali

• It’s The End Of The World As We Know It | REM: Keira Havens

• Free Bird | Lynyrd Skynyrd: Emily Berge

• This Must be the Place | Talking Heads: Lindsey Hall

• Money for Nothing | Dire Straits: Libbie Grant

• Goody Two Shoes | Adam Ant: Dana DuBois

• Like a Virgin | Madonna: Rachel Kramer Bussel

• Stay (I Missed You) | Lisa Loeb & Nine Stories Sari Botton

• 867-5309/Jenny | Tommy Tutone: Shelby Campbell

• Crazy Train | Ozzy Osbourne Ericka Kopp for VA-01

• My Sharona | The Knack: Courtney Kocak

• Rock Lobster | B-52’s: The Broom Closet Briefing

• Open | Regina Spektor Betsy Chasse

• Fall on Me | REM Jane Pratt

• Take on Me | ah-ha: ShālahBPookie - TheRebelCrone

• The Safety Dance | Men Without Hats: Amy Gabrielle

• Alive | Pearl Jam/ Pigs in Zen | Jane’s Addiction: Laura LeBleu

• Regret | New Order Paul von Zielbauer

• Baby Got Back | Sir Mix-A-Lot: Cass

• Everybody Hurts | REM: Tiffany Torres Williams

• Party All the Time | Eddie Murphy: Nicole Walters

• Wide Open Spaces | The Chicks: Dana VonAllmen

• Purple Rain | Prince and the Revolution: Karen Marie Shelton, Dana Walker Inskeep

• Iris | The Goo Goo Dolls ProfessorMeredith

• What’s On Your Mind (Pure Energy) Information Society Ayana Madrone 🌻

• Thorn in My Pride | The Black Crowes Nieta Greene

• One of Us | Joan Osborne; Seether | Veruca Salt God

I’ve tried my best to tag everyone who’s contributed so far. If I missed anyone, please let me know!