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Wealthy American Tony Hendon, has been accidentally shot and killed by his short-sighted mistress, Rita La Porta. He has left his $6 million estate to a hitherto unknown relative, Harry Witherspoon, an English shoe salesman - but there is one condition: Uncle Tony had always wanted to see Monte Carlo - and Harry has to take the corpse there in a wheelchair and must carry out Uncle Tony’s last wishes to the letter - exactly as detailed on an accompanying cassette tape. If he fails in any of the wishes, the money goes to the dogs’ home. Annabel Glick from the dogs’ home is secretly pursuing him, hoping he will mess it up. He is also secretly pursued by Rita and her optician brother, Vinnie, hoping to get their hands on missing diamonds they think are hidden on the corpse. The plot thickens with the entry of a sexy cabaret singer named Dominique du Monaco who is stalking Harry, and gets even thicker with mistaken identity, double-crossing, Rita disguised as a French Maid, and a surprise ending.

1983 novel The Man Who Broke the Bank at Monte Carlo by Michael Butterworth

LUCKY STIFF was the first Ahrens and Flaherty show to be produced. After hearing some of their work at an ASCAP songwriter's showcase, Ira Weitzman, head of musical theater development for Playwrights Horizons, invited the then-unknown team to work with him. After Ahrens and Flaherty won the prestigious Richard Rodgers Award, Playwrights Horizons (then under the artistic direction of Andre Bishop) agreed to produce it.

LUCKY STIFF premiered on April 26, 1988, and was enthusiastically received. The original cast included Stephen Stout, Stuart Zagnit, Mary Testa and Julie White. In 1990, the show was presented regionally at the Olney Theater in Maryland, and was awarded the Helen Hayes Award for Best Musical. That production starred Evan Pappas, who would later re-team with Ahrens and Flaherty for MY FAVORITE YEAR.

In 1993, six years after the show debuted, a cast album was finally produced and released on Varese Sarabande. Evan Pappas and Mary Testa reprised their roles, joined by Judy Blazer, Jason Graae and Barbara Rosenblat. The CD led to many more regional productions of the show.

In 2003, LUCKY STIFF was seen in New York for the first time since its original mounting, as part of the York Theater's popular Musicals in Mufti series. Five members of the original off-Broadway cast returned to revisit the show, and were joined by Malcolm Gets and Janet Metz as the show's leads. The five performance run was directed by longtime Ahrens and Flaherty colleague Graciela Daniele, and was one of the most well-received shows of the Mufti series. The York Theater mounting also resulted in a second cast recording on JAY Records, making LUCKY STIFF one of the few off-Broadway shows to boast two recordings of its charming and witty score.

Act I
• Something Funny's Going On - Company
• Mr. Witherspoon's Friday Night - Harry, Landlady, Telegram Deliverer, Spinster, Lorry Driver, Punk
• Rita's Confession - Rita and Vinnie
• Good To Be Alive - Harry, Luigi, and Company
• Lucky - Harry
• Dogs Vs. You - Harry and Annabel
• The Phone Call - Vinnie
• A Day Around Town (Dance) - Company
• Monte Carlo! - Emcee
• Speaking French - Dominique du Monaco
• Times Like This - Annabel
• Monte Carlo! (Reprise) - Emcee
• Fancy Meeting You Here - Rita
• Act I Finale: Good To Be Alive – Company

Act II
• Something Funny's Going On (Reprise) - Company
• Him, Them, It, Her - Harry, Annabel, Rita, Vinnie, and Company
• Nice - Annabel and Harry
• Welcome Back, Mr. Witherspoon - Company
• A Woman In My Bathroom - Harry
• Nice (Reprise) - Harry and Annabel
• Confession #2 (Reprise) - Tony, Rita, Harry, and Annabel
• Fancy Meeting You Here (Reprise) - Rita and Tony
• Act II Finale: Good To Be Alive - Company

Harry Witherspoon - a shy English shoe salesman
Annabel Glick - a no-nonsense representative of the Universal Dog Home of Brooklyn
Rita LaPorta - the high-strung lover of the dead Tony Hendon
Vinnie DiRuzzio - Rita's mild-mannered brother; an optometrist
Luigi Gaudi - a mysterious, boisterous Italian
Dominique du Monaco - a seductive French nightclub singer
Emcee - the emcee of a glitzy Monte Carlo nightclub
The dead body of Anthony Hendon - the corpse of Harry's uncle, fixed up so he looks alive
Landlady - the mean-spirited owner of Harry's apartment house

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