#11: Luck Be a Lady — Seal
Frank Loesser wrote this for the 1950 Broadway production of Guys and Dolls, and Sinatra’s recording for the 1955 film became the most famous version. Seal’s recording applied modern vocal production and genuine power to a song that rewards a big voice. He respected the big-band tradition while adding a soulful muscularity that Sinatra’s version, for all its authority, did not require. It is among the more straightforwardly successful entries on this list: a great song given to a singer capable of honoring it without needing to deconstruct it.

