Not specifically to do with singing - This video (link above) is nevertheless interesting for its candid perspective on show business. Many people who have only a passing acquaintance with Dave Chappelle might even be surprised to know that he had ever been a guest on Inside the Actor's Studio, but he proved to be one of the most interesting. So much so that when filming the 200th episode, with himself as the guest, James Lipton requested Dave Chappelle to be the host!
Here, though presented through the lens of comedy and Hollywood, Chappelle articulates with refreshing honesty many themes that will be familiar to those in other arenas of the performing arts: finding your medium, dealing with failure, the pressures of success, the lure of substance use and abuse, the sometimes corrupting influences in the business, the cost of fame, balancing personal and professional life, and the desire to communicate.
Full of both laughs and thoughtfulness, all in Chappelle's casual, sometimes crude style, it will nevertheless leave almost any watcher with a new appreciation for aspects of the life of a performer, as well as for this comedian, who is arguably one of the most astute social observers on the comedy circuit. Enjoy!