Google the phrase "gangsta Nancy Sinatra," and all search results lead back to Lana. By the time the press came calling, Del Rey was "a little embarrassed" by the comparison. ("That was supposed to be a joke," she told British GQ). Favoring a low voice and massive musical backdrops did echo Sinatra's stylish run in the swinging Sixties, so it's easy to see why the tag stuck. For her part, the daughter of Frank Sinatra, who’s best known for her no-nonsense hit "These Boots Are Made for Walkin'," is an O.G. for setting her own brash career agenda. (She shared one of the first interracial kisses on TV with Sammy Davis, Jr., and posed for Playboy in her 50s.) Last year, Del Rey and ex-boyfriend Barrie-James O’Neill covered "Summer Wine," a duet made famous by Sinatra and Lee Hazlewood in 1967.