487: Paul McCartney Is With My Ex and Why Keith Chase Hates Long Island

Why does comedian Keith Chase (@ChaseTheShortGuy) hate Long Island — even though he grew up in one of its wealthier communities? Tom Kelly sits down with fellow Long Island comedian Keith Chase on New York City's Upper West Side for a funny, surprisingly personal conversation about growing up in Roslyn, Long Island stereotypes, wealth, privilege, community, politics and getting outside the bubble you grew up in. First, Tom and Keith get distracted by the unusual connection between Paul McCartney, Nancy Shevell and Nassau County Executive/Governor candidate Bruce Blakeman. Keith also gives possibly the most controversial ranking of The Beatles ever attempted on a podcast. Pasted text Then Keith explains what he disliked about growing up in Roslyn: the money, status competition, entitlement and feeling that everyone was trying to prove they'd "made it." But he also talks about the advantages he had, the teachers who influenced him and why he's grateful for the opportunities his hometown gave him. The conversation expands into Long Island culture, Massapequa vs. Roslyn, changing neighborhoods, why Keith doesn't want to move back to Long Island, and how leaving his hometown bubble changed the way he sees the world. Timestamps 00:00 Paul McCartney, Bruce Blakeman & What's Coming Up 00:27 Comedian Keith Chase Joins The Tom Kelly Show 01:15 The Paul McCartney–Bruce Blakeman Connection 02:16 Tom's Encounter With Bruce Blakeman in Sag Harbor 02:40 Why It's Dangerous for Creators to Talk Politics 03:39 How Nancy Shevell Ended Up With Paul McCartney 05:53 Would You Rather Your Ex Leave You for a Beatle? 06:21 Keith Ranks The Beatles From Best to Worst 08:33 Keith's Advice for Bruce Blakeman 09:25 Tom's Strange Tom Brady Connection 10:59 Massapequa vs. Roslyn 12:31 What Does Keith Hate About Roslyn? 13:22 The "I Made It, So I'm Better Than You" Attitude 14:08 Working as a Lifeguard in East Hills 16:00 When Adults Bully the Lifeguards 17:07 What Keith Actually Loved About Roslyn 17:35 The Teachers Who Changed His Life 18:31 Leaving the Family Home Behind 19:38 How Roslyn Became a Jewish Long Island Suburb 20:35 Roslyn's Connection to the Man Who Built Levittown 21:18 Would Keith Ever Move Back to Long Island? 21:37 What Keith Hates About Long Island Culture 22:18 Long Island vs. Jersey, Westchester & Connecticut 23:36 How Did Long Island Prepare Keith for the Real World? 23:57 Escaping the Roslyn Bubble 25:10 Massapequa's Version of the Long Island Bubble 25:42 The Childhood Tragedy That Changed Keith's Perspective 27:01 Tom's Very Different Massapequa Experience 27:36 How New Yorkers Respond to Tragedy 28:25 Why Keith Needed to Get Out and See the World Follow Tom Kelly: @TomKellyShow Follow Keith Chase: @ChaseTheShortGuy