My Friend Irma (1949)

The storyline follows two women, Irma Peterson (Marie Wilson) and Jane Stacey (Diana Lynn), who room together in New York. Irma is a somewhat dim-witted blonde who deep down has good intentions. Jane is an amibitious woman who dreams of marrying a rich man. She winds up as a secretary for a millionaire, Richard Rhinelander (Don DeFore).

Meanwhile, Irma is in love with Al (John Lund), who is a con-artist looking to get rich quick. Al visits an orange-juice stand and encounters Steve Laird (Dean Martin) singing. He convinces him to leave his job and promises to make him famous. Steve and his partner Seymour (Jerry Lewis) then wind up living at Irma & Jane's apartment through the invitation of Al. She is angry, but Irma convinces her to let them stay. This opens up a romantic arc where Jane and Steve fall in love.

After a successful singing debut, Steve gets upset with Jane's wishes to marry a wealthy man and he leaves and returns to the juice stand. Meanwhile, Irma gets into a situation and decides to end her life. However, she finds out a radio station is about to call her for a $50,000 question, so she rushes home to answer the question. She wins the prize and all live happily ever after.