Dusty Reilly and Dude Cowan enjoy carefree lives riding the rails, with nothing to tie them down other than their friendship. Arriving in a small town, the two are lovestruck by a pair of gorgeous waitresses. Suddenly their hobo lifestyle no longer seems so appealing, and formerly minor details like money and personal hygiene become important. A high-stakes craps game against a gang of thugs offers Dusty and Dude the chance to marry their sweethearts. But whichever way the dice roll, it's not just their love lives at stake, since their opponents are very sore losers...
Though they are better remembered today for the long careers they enjoyed on their own, stars James Gleason and Robert Armstrong were considered inseparable by the public at the time of Oh, Yeah?'s release. The two actors began their association by co-starring in the hit Broadway play Is Zat So? in 1925. The two proved so popular as a comedy team that they were given their own radio series, Knights of the Road (in which they played characters similar to those in Oh, Yeah?) in 1931. Gleason subsequently found great success as a character actor, with memorable supporting parts in classics like Here Comes Mr. Jordan (1941), Arsenic and Old Lace (1944) and The Night of the Hunter (1955). Armstrong would be immortalized for his role as entrepreneur Carl Denham in King Kong and its sequel The Son of Kong (both 1933). Considered "the greatest dramatic actress" by Erich von Stroheim, ZaSu Pitts had been the star of the director's epic Greed (1924). Finding the transition to talkies difficult (her scenes in All Quiet on the Western Front in 1930 were deleted), Pitts developed a spinster persona that served her well in comedy roles for decades in everything from Life with Father (1947) to The Gale Storm Show (1956-1960).