The story is a modern retelling of the Faust legend[1] set during the 1950s in Washington, D.C., during a time when the New York Yankees dominated Major League Baseball.

Middle-aged real estate agent Joe Boyd is a long-suffering fan of the pathetic Washington Senators baseball team.

After she has gone to bed, he sits up late, grumbling that if the Senators just had a "long ball hitter" they could beat "those damn Yankees".

Fearful of losing his deal, Applegate calls Lola, "the best homewrecker on [his] staff", to seduce Joe and ensure his loss of the bet.

She promises to deliver ("A Little Brains, A Little Talent"), and Applegate introduces her as a sultry South American dancer named "Señorita Lolita Banana".

He releases false information about Joe's true identity being "Shifty McCoy", an escaped criminal and con artist.

Meanwhile, Applegate is exhausted by the work he has put into winning one bet and thinks about the "simpler" times in his long history ("Those Were the Good Old Days").

The owner of the Senators, their coach, and even Lola (disguised as "Señora McCoy") testify, but their opinions carry no weight.

Applegate claims that Joe "just needs time to think" and sends him to where Lola is, where history's most famous lovers wait.

The producers Frederick Brisson, Robert E. Griffith and Harold S. Prince[2] had decided that the lead actress for the part of "Lola" had to be a dancer.

The show starred Ray Walston (Applegate), Verdon (Lola), Shannon Bolin (Meg), Robert Shafer (Joe Boyd), Elizabeth Howell (Doris), Stephen Douglass (Joe Hardy), Al Lanti (Henry), Eddie Phillips (Sohovik), Nathaniel Frey (Smokey), Albert Linville (Vernon, Postmaster), Russ Brown (Van Buren), Jimmy Komack (Rocky), Rae Allen (Gloria), Cherry Davis (Teenager), Del Horstmann (Lynch, Commissioner), Richard Bishop (Welch), Janie Janvier (Miss Weston), and Jean Stapleton (Sister).

[4] It starred Olympic skater Belita (aka Gladys Lyne Jepson-Turner) as Lola, but the Fosse choreography was alien to her style, and she was replaced by Elizabeth Seal.

Garber was succeeded by Jerry Lewis, making his Broadway debut, on March 12, 1995,[7] who then starred in a national tour and also played the role in a London production.

[8][7] The 1994 revival production opened in the West End at the Adelphi Theatre on June 4, 1997 (previews started May 29) and closed on August 9, 1997.

[9] In 2006, North Shore Music Theatre in Beverly, Massachusetts, presented a revised production with the Washington Senators replaced with the Yankees' traditional rivals, the Boston Red Sox.

Jason Alexander directed, resetting the show to 1981 Los Angeles and making changes to accommodate a largely African-American and Hispanic cast.

It starred Jane Krakowski as Lola, Sean Hayes as Applegate, Randy Graff as Meg, Megan Lawrence as Gloria Thorpe (replacing an injured Ana Gasteyer during rehearsal), P. J. Benjamin as Joe Boyd, and Cheyenne Jackson as Joe Hardy.

It starred Stephen Bogardus as Joe Boyd, Matthew Morrison as Joe Hardy, Victoria Clark as Meg, Maggie Gyllenhaal as Lola, Whoopi Goldberg as a gender-bent Applegate, Danny Burnstein as Van Buren, and Adrienne Warren as Gloria.

[22][23] In 1983, Ray Walston expressed interest in recreating Applegate in Raisin' Cane, a new musical in which the devil returns to ruin Broadway.

In a spin on Damn Yankees, this time Applegate takes a young girl and grows her up and gets her the lead in a Broadway show, planning to change her back, bankrupting all the investors.

In 2009, it was announced that a new contemporary film adaptation of the musical will star Jim Carrey as Applegate and Jake Gyllenhaal as Joe Hardy.