Topic: Comedy
Where to Find It: iTunes

"True Tales Boldly Told" is the tagline of this hilarious show, hosted by comedian and writer Kevin Allison. This monthly live show is like a game of Truth AND Dare, as it gets people to put aside their fears and share real-life stories they normally wouldn't to a large audience. With high-profile, comedic guests like Sarah Silverman, Margaret Cho, Rachel Dratch, and Marc Maron, Risk!—at times shocking, at times touching, at times both—is a guaranteed fun time.