However, he expressed there were sometimes difficulties obtaining the licensing for some of the songs, given the age of the recordings and their legal rights status. He then cites the unusually cheery nature of Patti Page's 'Doggie in the Window' playing against 'dark and violent sequence' as well as Tchaikovsky's 'Waltz of the Flowers' playing against the crazed actions of Sander Cohen's Fort Frolic. For the songs that fit perfectly, he mentions Django Reinhardt's and Stéphane Grappelli's 'La Mer'. And sometimes playing against the scene can be a good thing.' In an interview, Levine commented that 'The question usually is: are you supporting the scene or are you playing against the scene. Levine was also inspired to include Django Reinhardt's recordings, in particular 'La Mer', after hearing his music in the 1999 film Sweet and Lowdown and in the 2002 video game Mafia: The City of Lost Heaven. He emphasized that the music came from the pre-rock 'n roll era including the work of artists such as Johnnie Ray, Rosemary Clooney, Patti Page, and Billie Holiday. Other songs were chosen by creative director Ken Levine who researched music with the help of his dad and through iTunes.

The licensed songs designed to be source music as if heard by the characters emanating from radios, phonographs, and jukeboxes rather than as incidental music heard from the game's score. In an interview, Ridgway explains 'The songs themselves, there's a really interesting juxtaposition of.a happy quirky musical.razzle dazzle number and then.they'd be singing about.how the world is ending.It was supposed to mirror the optimism and the decay at the same time.those two things sort of coexisting with each other.'

Several of the songs were chosen from Emily Ridgway's personal record collection, which included the artists Django Reinhart, Bing Crosby, and Noël Coward.

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