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* HoYay: He and many of his friends weren't shy about inserting blatant homoerotic subtext into their performances to the delight of audiences. He and Creator/JerryLewis frequently used this gag during their time as a double act. He also did a sketch with Music/FrankSinatra [[https://www.youtube.com/watch?v=VosG12PGGxM about the two of them being matched by a computer dating service]]. Rather curiously, the [[https://archive.org/details/DeanMartinFBI/page/n7 FBI's file on Dean Martin]] mentions "unsubstantiated information" from "an admitted homosexual" that he and another person whose name is redacted in the file (possibly Jerry Lewis?) were "known as gay". Jumping to conclusions a little, perhaps?
* VindicatedByHistory: "Ain't That a Kick in the Head?", one of Dean's iconic tunes, was originally released on a single that failed to chart despite strong reviews. Nevertheless, it grew in popularity over the years to the point that it's now a fixture on his {{Greatest Hits album}}s despite never having been a hit technically.
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