Dave and Milt break down the most memorable musical moments and controversies from the iconic Saturday Night Live. They discuss specific incidents including Sinead O'Connor's Pope photo-tear, Ashlee Simpson’s lip-sync debacle, and Rage Against the Machine’s protest, as well as touching on SNL's influence on modern comedy and music trends. The hosts also offer hot takes and personal insights, such as suggesting Justin Timberlake should join the SNL cast and arguing Andy Samberg’s superior comedic talent over Adam Sandler's. They conclude with a tribute to Paul Simon's poignant post-9/11 performance of 'The Boxer,' which they deem the most significant moment in SNL's history.

Topics

01:19 Listener Email: Bruce's Resignation

02:49 Kanye West and Documentary Discussion

06:15 Hot Takes on SNL Music Documentary

06:47 Mike Myers and Justin Timberlake on SNL

17:13 Ashlee Simpson's Lip Sync Incident

21:17 Sinead O'Connor's Controversial Performance

26:12 Elvis Costello and Fear's Performances

38:50 Saturday Night Live Trivia

39:48 Musical Guests Who Never Appeared on SNL

41:33 Rage Against the Machine Controversy

47:14 Kanye West's Antics

51:53 Eddie Murphy's Musical Comedy

56:19 Andy Samberg vs. Adam Sandler

01:02:40 The Influence of Lonely Island

01:10:45 Paul Simon's Post-9/11 Performance

01:15:03 Final Thoughts and Wrap-Up