I like podcasts about music and movies:
How Did This Get Made? (discussing crazy movies)
Newcomers (watching popular film franchises for the first time)
Song Exploder (songwriters discuss their creative process)
Doug Loves Movies (comedians play movie trivia games)
Pop Culture Happy Hour (a daily discussion of the latest movies, TV shows, music and books)
Also check out Waiting for Impact, a limited series that ran last fall wherein former MTV VJ Dave Holmes tracks down a mysterious 90's boy band and reflects on the unexpected paths our lives can take.