Roosevelt Hotel

The Hollywood Roosevelt Hotel is legendary in Tinseltown, not only because it hosted the first Academy Awards in 1929. Clark Gable and Carole Lombard hooked up in the penthouse, and Marilyn Monroe lived at the hotel and did her first modeling photo shoot there. After a major remodeling in 2005, the Roosevelt, its VIP club Teddy’s and its poolside Tropicana Bar once again became the Hollywood hangout. Kirsten Dunst is a regular Tropicana dweller although she apparently curtailed her fully-clothed swimming adventures and the list of celebs who’ve lounged poolside reads like an Oscar Night red-carpet rundown: Bruce Willis, Lindsay Lohan, Jessica Simpson, Tobey Maguire, Jake Gyllenhaal, Prince, to name a few. Towering palm trees and teakwood furniture surround the pool, famous for its David Hockney mural. Guests have been known to make reservations several months in advance to reserve one of the cabana rooms, so unless your name happens to be Justin Timberlake, plan ahead. If you show up at night, improve your chance of entry by coming with a pack of pretty girls, not eight golfing buddies, to lounge around the fire pits near the bar. Los Angeles-area DJs spin downtempo tunes, and the vibe is surprisingly laid-back for such an exclusive spot. With a few design tweaks to the Tropicana Bar area, they’re now serving dinner from the hotel’s five-star Dakota restaurant. But at this ultra-cool poolside bar, food will be the last thing on your mind.