This singer played a detective in 3 straight 60's films: "Tony Rome", "The Detective" & "Lady in Cement"
The Detective [1968] [DVD] by Jim Inman DVD 4.84 
... DVD Release Date: 3 July 2006; Run Time: 110 minutes; Average Customer .... 
tricks from old "film noirs" from 40s and 50s, but adds to it some flavours from 60s
... [DOC] [TLE] Frank Sinatra - Wikipedia [PAR] Francis Albert "Frank" Sinatra was an American singer, actor, and producer who 
was one of the ... Sinatra forged a highly successful career as a film actor.