The night before the thrilling come-from-behind victory of Street Sense at this year's Kentucky Derby, Playboy turned Louisville's Mellwood Arts and Entertainment Center into the Crown Royal Playboy Lounge for the weekend's biggest party. Newly crowned Playmate of the Year Sara Jean Underwood played host to a stable of celebs like 8 Mile's Brittany Murphy, Brothers & Sisters star Jason Lewis, NFL great Tom Brady, 24's D.B. Woodside and many more, who all grooved to legendary New York turntablist Semu "DJ Reach" Namakajo. Hundreds of lucky guests sipped Crown Royal cocktails amid gorgeous Playmates and Bunnies late into the night before the historic Run for the Roses -- and they all walked away winners.

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Photography by James Trevenen