Charles Walters, announced as the director, bowed out of the project when his first choice for lead actress, June Allyson, lost the part to Susan Hayward. Upon her casting, Miss Hayward requested Daniel Mann to direct, and Susan also wanted and received script revisions.
Lillian Roth was disappointed that MGM did not ask her to sing for Susan Hayward on the soundtrack. Coordinated with the movie's release, Epic Records issued an album of Lillian reprising tunes associated with her career in vaudeville, on Broadway and in Hollywood. Containing 12 songs with an orchestra directed by Don Costa, the album used the same title ("I'll Cry Tomorrow") as Miss Roth's 1954 autobiography (co-written with Mike Connolly and Gerold Frank), plus the 1955 biopic. Miss Roth's LP contained the three complete numbers performed by Susan in the movie: "Sing You Sinners," "When the Red, Red Robin Comes Bob, Bob, Bobbin' Along" and "Happiness Is a Thing Called Joe." Lillian's LP did not include "The Vagabond King Waltz" (sung partially on screen by Miss Hayward) nor the film's promotional song (music by Alex North, lyrics by Johnny Mercer), a mournful ballad introduced on disc by Susan, who was backed by Johnny Green and His Quartette. Initially, the Hayward cut was released by MGM Records on both a 45-rpm single
Appearing together for the only time on film were Eddie Albert (playing Burt McGuire) and his wife Margo (portraying Selma). The couple were wed from December 5, 1945 until Margo's death on July 17, 1985.
Earning nearly $8,000,000, this picture became the fourth-highest moneymaker of 1956.
Hollywood actresses in contention to play Lillian Roth included June Allyson (who nearly won the role), Grace Kelly, Janet Leigh, Jane Wyman, Jean Simmons, Jane Russell and Piper Laurie.
In her second autobiography published in 1958, "Beyond My Worth," Lillian Roth noted that although her mother Katie spoke with a Boston accent, Jo Van Fleet portrayed Katie as sounding ethnically Eastern European Jewish.
In his autobiography, writer Arthur Laurents, who worked with Lillian Roth when she was in his 1962 play "I Can Get It for You Wholesale," said that contrary to this movie's happy and romantic ending for Burt and Lillian, the real-life Burt left Lillian for a man a few years after the movie was released.
In its poster art for the film, MGM proclaimed that "Susan Hayward Sings" -- in a similar vein to the studio's earlier "Garbo Talks" slogan for Anna Christie.
In March 1955, The Hollywood Reporter wrote that nine-year-old Lana Wood had tested to play Lillian Roth as a child. In May, the trade paper noted that Thelma Ritter was being considered for the role of Lillian's mother Katie.
MGM had hired vocalist Sandy Ellis to sing for Susan Hayward, but after listening to Miss Hayward's rehearsal tracks, the movie's creative team chose instead to use her own singing voice, which had been dubbed earlier by Peg La Centra in Smash-Up: The Story of a Woman, then by Jane Froman in With a Song in My Heart, and later would be dubbed by Margaret Whiting in Valley of the Dolls. Initially, Miss Ellis had prerecorded two standards: "When the Red, Red Robin Comes Bob, Bob, Bobbin' Along" (music and lyrics by Harry M. Woods) and "Happiness Is a Thing Called Joe" (music by Harold Arlen, music by E.Y. Harburg). Both Ellis tracks plus all the Hayward vocals are featured on the complete soundtrack CD issued by Film Score Monthly in 2004.
On the six-selection "I'll Cry Tomorrow" EP, issued by MGM Records in conjunction with the film's opening, Susan Hayward sings one chorus of "I'm Sitting on Top of the World" (music by Ray Henderson, lyrics by Sam Lewis). This upbeat ditty is not performed by Miss Hayward in the release print. Susan's recording was reissued in 2004 on the deluxe soundtrack CD from Film Score Monthly.
Pryor to filming, Susan Hayward took the opportunity to study Lillian Roth's vocal style, tone and delivery when Miss Roth performed in Las Vegas. Moreover, the two women became friends during the production.