The Toss Up

The Toss Up

The Toss Up is a rapid-fire interview/game show featuring two guests every week. Over the course of four cutthroat trivia and puzzle games, the players compete for a donation to charity of their choice (and infinite bragging rights).

Episodes

March 24, 2025 34 mins

Tess Hurlburt & Kamiya Willoughby are back to reignite their rivalry in four games of horror and puzzles! Produced and Edited by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band // Support Us at Patreon.com/TheTossUp

Mark as Played

Meera Forespring and Tharu Lansakaranayake take to the stage in four fast games of puzzles, news, and Avatar: The Last Airbender! Produced and Edited by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band // Support Us at Patreon.com/TheTossUp

Mark as Played
March 2, 2025 33 mins

Kenny Jones and Katie Timzen face off in four games of music, movies, and mind-melding puzzles! Produced and Edited by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band // Support Us at Patreon.com/TheTossUp

Mark as Played
February 23, 2025 40 mins

Nick Curl returns with known roommate Jack Seligmann for four fast games of news, movies, and cooking. Produced and Edited by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band // Support Us at Patreon.com/TheTossUp

Mark as Played
February 16, 2025 37 mins

Sarah Frasco and Cara Larson are back to duke it out over four games of sports, TV, and YA Literature. Produced and Edited by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band // Support Us at Patreon.com/TheTossUp

Mark as Played
February 9, 2025 37 mins

Ben Goodwin and David Zuckerman flex their trivia skills in four games of myth and fantasy. Produced and Edited by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band // Support Us at Patreon.com/TheTossUp

Mark as Played
January 26, 2025 46 mins

Multi-hyphenate creatives Ivy Penn and Joi Pierre go head-to-head in four rounds of news, Disney, and puzzles. Produced and Edited by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band // Support Us at Patreon.com/TheTossUp

Mark as Played
January 19, 2025 31 mins
TWO BROTHERS Andrew and Mitch face off for sibling supremacy in four cutthroat games of news, Nintendo, and mental health trivia. Produced and Edited by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band // Support Us at Patreon.com/TheTossUp
Mark as Played
January 12, 2025 37 mins
Joey Carlson and Zoë Hughes return for a wild romp through history, television and Minecraft! Produced and Edited by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band // Support Us at Patreon.com/TheTossUp
Mark as Played
January 5, 2025 51 mins
Aaron Hluch and Davis Grant are back for their latest battle for trivia stardom! Edited and Produced by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band// Support Us at Patreon.com/TheTossUp
Mark as Played
April 22, 2024 58 mins
Keya Vance and James Williams are no strangers to horror. They sus out spooky supernatural celebrity stories in this cutthroat competition! Edited and Produced by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band
Mark as Played
April 14, 2024 42 mins
Will Lebowitz and Joseph Mueller step up to test their fandom knowledge across five games of Star Wars, Video Games, and DC comics! Edited and Produced by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band
Mark as Played
March 17, 2024 53 mins
Newly betrothed Coco Harshbarger and Nathan Weinreich put their knowledge of history and Old Hollywood to the test in five game of trivia. Edited and Produced by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band
Mark as Played
February 26, 2024 51 mins
Davis Grant and Aaron Hluch return to the arena to decide which contestant is the most insufferable victor. Edited and Produced by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band
Mark as Played
February 18, 2024 46 mins
Get ready for an adolescent throwback between Sarah Frasco and Cara Larson as they butt heads through five games of 2010s pop, Twilight, and Sex and the City. Edited and Produced by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band
Mark as Played
February 11, 2024 59 mins
Louisa Rorschach and Kate Rafter square off in an epic battle of hyperactive minds through five games of science, entertainment, and People's Princess trivia. Edited and Produced by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band
Mark as Played
February 3, 2024 53 mins
Calvin Bruhns and Olga Tambazidis try their luck at five games of Religious History, Actors, and 2010s Trends. Who will become the cheugy champion? Edited and Produced by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band
Mark as Played
January 27, 2024 57 mins
Anju Endo, Nana Okamoto, and Kamiya Willoughby aren't here to make friends. Only one trivia champ will be crowned victor! Edited and Produced by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band
Mark as Played
January 20, 2024 48 mins
Keith and Sarah Currivean square off to see who's the better cat parent, news junkie, and Texan in five games of trivia. Edited and Produced by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band
Mark as Played
January 15, 2024 59 mins
Abe Luedtke and Nathan Ward parse fact from fiction in five games of science, rock climbing, and everything in between. Edited and Produced by Simon Leftie // Artwork by Max Kolomatsky // Music by Jacob Mann Big Band
Mark as Played

Popular Podcasts

    I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

    Dateline NBC

    Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Special Summer Offer: Exclusively on Apple Podcasts, try our Dateline Premium subscription completely free for one month! With Dateline Premium, you get every episode ad-free plus exclusive bonus content.

    24/7 News: The Latest

    The latest news in 4 minutes updated every hour, every day.

    The Breakfast Club

    The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

    The Joe Rogan Experience

    The official podcast of comedian Joe Rogan.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.