11. P.J. Clarke’s (1884)
Some restaurants may be older than this homey burger bar, but few have as impressive a lineup of famous diners as P.J. Clarke’s. Its website quotes Nat King Cole, who called its burger “the Cadillac of burgers,” and says that “Buddy Holly proposed to his wife here five hours after they met.”
The pub got its start in 1884 serving beer to Irish immigrants, and became even more popular during Prohibition when it illegally brewed and imported gin and scotch. From then on, P.J.’s wormed its way into the hearts of multiple stars, like Frank Sinatra, Jackie O, Peter O’Toole, Elizabeth Taylor, and Johnny Mercer. (The bar is almost certainly the inspiration for the boozy ballad “One for My Baby,” which Mercer wrote on the back of a napkin in the restaurant.) Author Charles Jackson also penned The Lost Weekend while dining here, and the motion picture on which it was based was filmed on a Hollywood set modeled after P.J. Clarke’s. It was also a filming location for Mad Men and Annie Hall.
When the property was finally sold by the Lavezzos in 1967, a 99-year leaseback was included. So, go try the burger loved around Hollywood, lest you regret it come 2066 when the lease expires.