The original cast assembled by Jason included: Marla Cáceres*, Alex EIlhauer, John P. Glynn, Sarah Haskins [Blackish (ABC), Booksmart (2019), 80 for Brady (2023)], Jordan Klepper [The Daily Show (Comedy Central), The Opposition w/Jordan Klepper (CC), The Ghost & Molly McGee (Disney+)], Arnie Niekamp [Jackbox Games], Eddie Piña*, Steve Waltien [The Colbert Report (CC), The Late Show w/Stephen Colbert (CBS), Don’t Think Twice (2016)], Shane Wilson*, and Matt Young. They were joined by Padraic Connelly shortly into the original run.

Originally scheduled for a limited run, the show was quickly extended by two months. And then another two months. And then another.

Now, 20 years later, the show is still doing another two months!

The show has been running since 2003 at the iO Theater in Chicago, IL: First at 3541 N. Clark Street, and then moving to their current home at 1501 N. Kingsbury. 

Over the years, the show has welcomed guest performers from film, television, radio, and even print media. Cast members added over the years include: The Katydids (creators of Teachers), Punam Patel, Patrick Rowland, Sarah Wonak, Atra Asdou, Brooke Breit, Brett Lyons, Megan O'Neill, and many more. Guest performers have included Marina Squerciati [Chicago P.D.], Sophia Bush [One Tree Hill], and local media legends Steve Dahl [Steve & Garry, "Disco Demolition Night"] and Derel Jevens [Chicago Sun-Times] to lend some journalistic integrity to the show.

The show has toured the U.S., including extended runs at the Piccolo Spoleto festival and the Temple Theater. The show also enjoyed a brief foray into the early days of streaming with an NBC pilot that the cast has collectively agreed never to mention again.

During its run at iO, Whirled News Tonight also produced WNT Late Edition, The Sarah Palin Show, and the quadrennial classic Electapalooza.