Frank Sinatra plays private eye Rocky Fortune, a "footloose and fancy-free young man," frequently unemployed, who would then take on a range of odd-jobs that would lead into adventurous escapades.

Rocky, always ready with a wise remark and a tongue-in-cheek approach, is a magnet for trouble. There is usually a beautiful woman involved; some good, some bad. His tough guy stays just inside the law, though we often get a glimpse of a soft heart beneath the hard-boiled exterior.

Rocky usually received job assignments from the Gridley Employment Agency, usually referred to as "the agency". During the series, he worked as a process server, museum tour guide, cabbie, bodyguard, chauffeur, truck driver, social director for a Catskills resort and a carny. He could also fake enough bass to play at weddings and bar-mitzvahs.

The show aired just as Sinatra was in the running for an Oscar for his role in 'From Here to Eternity', it became a running gag that Rocky seemed to work the phrase "from here to eternity" into almost every show.