See You in Jail (1927)

Jerry Marsden, the son of a wealthy man, finds himself in a series of comedic misunderstandings. To prove a point or escape a social obligation, Jerry decides to take the place of his butler, who has been sentenced to a short stay in jail. While incarcerated, Jerry finds the experience surprisingly pleasant, as he receives special treatment and even manages to flirt with the jailer's daughter, Ruth Morrisey (Alice Day). Chaos ensues when his true identity is threatened and he must navigate the complexities of high society while technically being a "prisoner."