73: Jack Antonoff of Bleachers, Fun, and Steel Train

Jack Antonoff of Bleachers, Fun, and Steel Train had very specific ideas of what success in the music industry looked like. When his band Fun blew up, it also blew up those ideas and expanded his horizons. In this conversation, we talk about that explosion, the writing process, and "buying the delusion" as an artist when no one else will believe in you.

65: Wyclef Jean

Wyclef Jean casts a big shadow in hip hop, R&B, and pop music. While The Fugees mega-hit "The Score" sold more records, his solo debut "The Carnival" is really what helped him cast that shadow. Some people have described it as a cold, calculated attempt by record execs to push urban music further into the mainstream. According to Wyclef, though, nobody knew if the record would even work!

56: Grandmaster Flash

Grandmaster Flash was more integral in the creation of hip hop as we know it today than any other individual. While many people know him as the man behind "The Message," his journey began over a decade earlier as a little kid from the Bronx who was obsessed with his dad's stereo.