Fourteen Lost Souls, Dept.
Right, so, Damn Yankees. Great, overlooked American musical film from the tail end of the Golden Age of Hollywood Musicals™. Rarely named among the genre's best despite powerhouse performances by Gwen Verdon as "Lola" and Ray Walston as "Applegate" (i.e., the Devil) and perennial showstoppers such as "Heart" and "Whatever Lola Wants."
At any rate, the last number in the film. "Two Lost Souls."
Exposition time: Joe Hardy, the middle-aged diehard Washington Senators fan who sold his soul to Applegate in exchange for a pennant for his hapless team and a lead role in the Senators' victory over the hated Yankees as a rejuvenated slugger, commiserates with Lola, who has fallen for the clean-cut Joe. Lola was once the "ugliest woman in Providence, Rhode Island," but was transformed into a bombshell (at the price of her soul) to help Applegate win men's souls. Joe is due to deliver his soul the next day, and the sympathetic Lola has done what she can to help him stay out of Applegate's clutches. They sit in the park, he despairs over his fate, they kiss, they adjourn to a bar for a tipsy dance number. End exposition.
"Two Lost Souls" has been done by a number of performers over the years, some not exactly representing the song's mixed tone of sadness, resignation and release.
So, that said, here's the original 1958 film version with Tab Hunter and Gwen Verdon.
Here are Jane Krakowski and Cheyenne Jackson in the 2008 Encores! series staging of Damn Yankees.
Here are Lee Remick and Jerry Lanning in a trippy, low-budget 1967 television staging.
Here are Liza Minnelli and Judy Garland doing the song in the tramp garb that the latter semi-regularly assumed in a 1963 television performance on The Judy Garland Show.
Here's a Muppet version, featuring Robin and Sweetums.
Here's a twofer: Jaye P. Morgan and Perry Como, the latter incapable of voicing despair in his buttery baritone, followed by Steve Lawrence and Eydie Gorme, who don't improve much on the tone, but do offer some nice harmony singing.
I'll spare you the many high school, college and community theater productions viewable on YT, but I will offer a special Sobsister Sunday Bonus: rehearsal footage, featuring Gwen Verdon and Chita Rivera, from the original run of Chicago. Pure gold, I tells ya.
Anyway, more versions than you'd like, but fewer than you need. Or vice versa.