Robin and the 7 Hoods OST

 (Reprise, 1964) Sinatra was the original Sandler, assembling his buddies to hang out on the set of a movie (and then not giving it the 100% "Man with the Golden Arm"/"Uncut Gems" effort). The most famous thing about this film is the introduction of "My Kind of Town," a song that seems both GOAT classic and weirdly lazy ("I saw a man, he danced with his wife"). It lost the Oscar for best song to Dick Van Dyke's singing chimney sweep. The second most famous thing about this movie is that Peter Lawford was kicked out of the Rat Pack for not interceding with his in-law JFK, who barred Sinatra from the White House for Frankie's real life gangster connections. Subsequently, Lawford was replaced by Bing Crosby in the move so he did not get to play an imaginary gangster in this picture. Sammy, btw, who was ostracized by the JFK administration for having a white wife, continued to work with Lawford years later. But that is about the movie and real life, let's talk about the soundtrack. Sinatra would actually get way better at singing "My Kind of Town" over the years, so even the highlight here is not a super highlight. They only let Peter Falk sing one song (likely because he sings like Columbo with a cold), Bing sings with kids, Dino sings about being a mother lover, and Sammy gets the goofy numbers, but unlike other Reprise ensemble projects, this musical is mostly goofy numbers, so he doesn't get them all. On "Mister Booze," a church revival preacher song Sammy testifies in the voice of Kingfish from "Amos and Andy." I don't mind when he does Kingfish as one of his many impressions, Kingfish was the Homer Simpson of his day, but here it feels like Sammy is already the token, so throwing in minstrelsy-adjacent stuff is icky (there is a blackface scene in the movie, where the white Hoods are putting brown shoe polish on to pull off a job, and Sammy makes a non-criticizing crack). "Bang Bang," his only solo, is silly and he throws more vocal mimicry in (in the movie there is dancing and production making it more memorable than on the recording). The finale is a reprise of not the actual hit song from the show but the dumb "Don't Be A Do-Badder," which is short and silly and Sammy doesn't really stand out. With the Rat Pack flicks Sinatra was hanging and banging with his buddies and was not out to make great art, and on this movie he achieved his goal...of not greatness.