In 2016, veteran Democratic advisor Philippe Reines stepped up for an unconventional task: impersonating Donald Trump for Hillary Clinton's debate prep. And in 2024, he did it all again for Kamala Harris. Jon Lovett and Reines discuss the intricacies of playing Trump, the impact of debate performance on elections, and what Democrats should do to outwit the president going forward. Reines reveals what really happened the night Biden called Harris moments before her debate, Trump's biggest debate weaknesses, and what it was like working with Lovett as a Clinton staffer back in 2005.
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Two Guys, Five Rings: Matt, Bowen & The Olympics
Two Guys (Bowen Yang and Matt Rogers). Five Rings (you know, from the Olympics logo). One essential podcast for the 2026 Milan-Cortina Winter Olympics. Bowen Yang (SNL, Wicked) and Matt Rogers (Palm Royale, No Good Deed) of Las Culturistas are back for a second season of Two Guys, Five Rings, a collaboration with NBC Sports and iHeartRadio. In this 15-episode event, Bowen and Matt discuss the top storylines, obsess over Italian culture, and find out what really goes on in the Olympic Village.
iHeartOlympics: The Latest
Listen to the latest news from the 2026 Winter Olympics.
Milan Cortina Winter Olympics
The 2026 Winter Olympics in Milan Cortina are here and have everyone talking. iHeartPodcasts is buzzing with content in honor of the XXV Winter Olympics We’re bringing you episodes from a variety of iHeartPodcast shows to help you keep up with the action. Follow Milan Cortina Winter Olympics so you don’t miss any coverage of the 2026 Winter Olympics, and if you like what you hear, be sure to follow each Podcast in the feed for more great content from iHeartPodcasts.