Lucky Break (2001) on Netflix

Plot summary

A botched bank robbery lands Jimmy Hands and his old friend Rudy Guscott in prison, and a transfer puts Jimmy somewhere he might be able to get out of. He persuades the governor to let the men put on a musical in an old chapel beside the outer wall, and recruits volunteer actors from the inmates; the show is cover for his escape plan. Jimmy is cast as Nelson against his will, Guscott as Hardy, and Cliff Gumbell, a fellow prisoner, volunteers at the piano. Two obstacles remain: John Toombes, a dangerous inmate who wants in on the escape, and Annabel Sweep, a social worker helping with the show, to whom Jimmy finds himself drawn.