Tin Cup · The Rewatchables ·September 16, 2025 Best Double Feature Tin Cup + The Thomas Crown Affair The Thomas Crown Affair Happy Gilmore Happy Gilmore Caddyshack Caddyshack In the discussion (1) Approx. transcript time · 01:50:45Read transcript Double features are The Thomas Crown Affair, Happy Gilmore and Caddyshack, with generational taste shaping the golf choices.