When Amber Ruffin was living in Omaha, Nebraska, she figured she’d stay there forever – carrying the mail, buying a home, and maybe doing some community theater. Then she attended the Chicago Improv Festival with her Omaha improv group, and decided to pack up and move to the Windy City and give full-time comedy a try. Sam asks her how she got from improv to hosting her own late night TV show, her Tony Award-winning turn as a Broadway writer, and how she finds her amazing wardrobe of suits.

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Postal Uniform or Power Suit? (with Amber Ruffin)