The Toss Up

Simon Leftie
  • 5.0 (1)
  • COMEDY INTERVIEWS
  • UPDATED WEEKLY

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).

  1. 58008

    03/24/2025

    58008

    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

    35 min
  2. A Charizard Cheetoh

    03/16/2025

    A Charizard Cheetoh

    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

    39 min
  3. A Cocaine Toupee

    03/02/2025

    A Cocaine Toupee

    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

    33 min
  4. Yankees on Steroids

    02/24/2025

    Yankees on Steroids

    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

    41 min
  5. Jesus of Narnia

    02/16/2025

    Jesus of Narnia

    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

    37 min
  6. Giants on Stilts

    02/10/2025

    Giants on Stilts

    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

    38 min
  7. Quasimodo's Hot Boy Summer

    01/26/2025

    Quasimodo's Hot Boy Summer

    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

    46 min
  8. A Thousand Years of Lobotomies

    01/20/2025

    A Thousand Years of Lobotomies

    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

    32 min
See All (43)

About

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).

Information

  • Creator
    Simon Leftie
  • Years Active
    2024 - 2025
  • Episodes
    43
  • Rating
    Clean
  • Copyright
    © Simon Leftie
  • Show Website
    The Toss Up