Pineapple Street Studios Launches New Season of Award-Winning, Critically Acclaimed Pop Culture Series “Back Issue"

On the weekly show launching February 21,Josh Gwynn reminisces on the formative moments in pop culture’s past that have shaped our present, joined by special guest co-hosts including Wesley Morris, Sam Sanders, Hunter Harris and Jazmine Hughes 

New York, NY (February 16, 2023)—Pineapple Street Studios, an Audacy company, today announced the launch of the third season of Back Issue, the award-winning, critically acclaimed original series hosted by Pineapple Street Studios Senior Producer Josh Gwynn in which he reminisces on formative moments in pop culture’s past that have shaped our present, rewinding on the things forgotten or things we can’t seem to ever forget with personal reflections, incredible guests, and plenty of deep belly laughs. 

This season, Season 1 and 2 co-pilot Tracy Clayton is taking a break, so Gwynn has invited some special guest co-hosts, including Wesley Morris, Aisha Harris, Hunter Harris, Sam Sanders, Ashley C. Ford, Matt Bellessai, Jazmine Hughes, BA Parker, Bobby Finger and Lindsey Weber to share their perspectives. Clayton will also be featured on two episodes. 

On Back Issue Season 3, Gwynn and friends will explore a wide range of cultural touch points and milestones, taking a deep dive into the what, how and why these moments impact culture as we know it today. Topics include: the gendered politics of specific hairstyles as Josh sets out on a mission to get a silk press; iconic award speeches; how the world of celebrity gossip has changed over the years, and the chemistry of what gossip does to our brains;  the backstories of Degrassi and Cheetah Girls; which multi-hyphenate performers are deserving of their flowers; an exploration of whether Gwynn should become the next Black ex-pat and more. 

Back Issue Season 3 will launch on February 21, 2023, on the Audacy app and everywhere podcasts are available. New episodes will be released Tuesdays throughout the season. Listen and follow the show here: Back Issue.

“I’m so excited that this season, we’re going to be able to get into all sorts of formative pop culture moments because we’re bringing on guests to expand the range of things we cover,” said Josh Gwynn. “I can’t wait for folks to hear all of the wit, knowledge, laughter and heart that everyone, and especially the production team, put into this brand new season.” 

“We’re so excited to have ‘Back Issue’ back in everyone’s ears,” said Jenna Weiss-Berman and Max Linsky, co-founders of Pineapple Street Studios. “It’s a show that audiences love — smart, honest, inspiring, funny as hell — and one that everyone at Pineapple is proud to put out into the world.”

The New York Times called Back Issue “a balm in trying times.” Back Issue was featured on  Time’s list of “The 10 Best Podcasts of 2020” and in the top 15 on The Atlantic’s “Best 50 Podcasts of 2020. Back Issue won the 2021 Webby Award in the Arts & Culture category  (People’s Choice winner), and the 2022 Ambies award for “Best Entertainment Podcast.” 

Back Issue was created by Josh Gwynn and Tracy Clayton, and hosted by Gwynn, who also serves as senior producer. The series is executive produced by Leila Day, produced by Janelle Anderson, Xandra Ellin, and Ari Saperstein; and edited by Day and Emmanuel Hapsis. Bria Mariette is the managing producer; sound engineers include Sharon Bardales, Davy Sumner, Jason Richards, Jade Brooks, Marina Paiz, Pedro Alvira and Raj Makhija. Executive Producers for Pineapple Street Studios are Jenna Weiss-Berman and Max Linsky. 

Josh Gwynn is a Senior Producer and host of Back Issue podcast at Pineapple Street Studios. He’s from Southern California and has created work for companies like The New York Times, Netflix, Essence, Stitcher, Mailchimp, and Nike. He is passionate about providing platforms for underserved voices. Josh received his Masters in Media Management from The New School/Parsons in New York City and is a graduate of Emory University in Atlanta. Given his California roots, Josh describes his vibe as a combination of palm trees, confetti, limes, rhythm, vitamin E oil, melanin, and bones. He is still waiting on a ticket to Oprah’s Legends Luncheon.

Download the cover art for Back Issue and Josh Gwynn’s photo [credit: Colby Blount] here.

Follow Back Issue on Instagram @BackIssuePodcast. Follow Josh Gwynn on Twitter @RegardingJosh and Instagram @RegardingJosh. Follow Pineapple Street Studios on Twitter @PineappleMedia and Instagram For more information, visit

About Audacy

Audacy, Inc. is a leading multi-platform audio content and entertainment company that connects with 200 million consumers. Powered by its exclusive, premium audio content that includes unrivaled leadership positions in news and sports radio, Audacy operates one of the country’s two scaled radio broadcasting groups, a rapidly growing direct-to-consumer digital audio platform, multiple audio networks, a major event business and a leading, award-winning podcast studio Learn more at, Facebook (Audacy Corp), X (@AudacyCorp), LinkedIn (@Audacy-Inc), Instagram (@lifeataudacy) and Threads (@AudacyCorp).

About Pineapple Street Studios

Founded in Brooklyn in 2016 by Jenna Weiss-Berman and Max Linsky, Pineapple Street Studios, an Audacy company, paved the way for in-depth, diverse storytelling by way of high-quality original and partner podcasts. Pineapple Street Studios creates inventive, award-winning original podcasts: multi-episode narratives, investigative journalism, branded series, and talk shows that routinely debut in the top ten on the Apple Podcasts charts, reach tens of millions of listeners, and have been cited repeatedly on “best-of” lists. Pineapple Street Studios is behind some of the most critically acclaimed shows, including Patrick Radden Keefe’s Wind of Change, Welcome to Your Fantasy, Missing Richard Simmons, Back Issue, The New York Times’ Still Processing, activist Brittany Packnett Cunningham’s Undistracted, and The Catch and Kill Podcast with Ronan Farrow.

Ready to Make Audio Work for Your Brand?