We Might Be Drunk Ep 266: Chelsea Handler
7 snips
Jan 12, 2026 
Chelsea Handler, a comedian and bestselling author, joins for a wild chat about her career feats and personal tales. She shares her experience hosting the Critics' Choice Awards and the freedom she finds in a nomadic lifestyle over traditional talk shows. Chelsea recalls her early career bomb in Montreal, discusses hilarious dating stories with celebrities, and dives into her gambling escapades. Her belief in independence shines through as she also reflects on her impact with 'Chelsea Lately' and her upcoming High and Mighty Tour.
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Rehearse, Then Stay Flexible
- If you do award-show monologues, rehearse a few times and stay flexible for last-minute changes.
- Chelsea Handler says write broadly and adapt on the fly so you can pivot for surprise audience members or absent nominees.
Podcasts Have Become Modern Talk Shows
- Talk shows as a format are shrinking while podcasts fill that conversational space.
- Chelsea Handler observes podcasts are becoming the talk shows that traditional TV no longer is.
Prioritize Personal Freedom
- Guard your freedom: design a career that doesn't tie you to one studio or city if independence matters.
- Chelsea Handler emphasizes choosing work that preserves mobility and autonomy.
