In the late 1930s, George Raft was at the top of the movie business. He had a lot of prestige at Warner Brothers and looked destined for greatness. However, after a very long string of insane career choices (rejecting the lead in such films as "High Sierra" and "The Maltese Falcon"--all of which made Bogart a top star), his clout suddenly vanished and he played out the 1940s in a string of progressively less prestigious and uninteresting films. When "Whistle Stop" debuted, he was already well on the way to becoming a second or third tier actor--and unfortunately, his performances generally looked second or third-rate as well. I've seen quite a few of these later films and can only describe his performances as 'wooden'.
"Whistle Stop" has a major handicap at the onset. Raft is cast opposite Ava Gardner as the love interest--though he was over 20 years older and seemed ill-suited and ill-at-ease in this romantic role. And, frankly, this wasn't all Raft's fault. I especially cringed at the flashback scene where they tried to make Raft and Gardner look like teenagers--his hairstyle was pretty funny and he looked like a 45 year-old man trying to be young and hip (which he was).
The film begins with Gardner returning to the small town where she grew up but had left in order to live in the excitement of Chicago. It soon becomes apparent that she and Raft (oddly cast as a small-town sort of guy) had a past history together...but was distracted by both the lure of Chicago and the tough and rich Tom Conway. And, ultimately, Conway and Raft fought it out for her. Raft won the fight, but she left with Conway...but now, years later, she is back. But can she pick up where she and Raft left off? One thing getting in their way is the directionless way Raft's life has become--as if he didn't care about tomorrow. Can he clean up his act and win the girl? And, will Conway make trouble for Raft now that he's apparently won Gardner? In addition to these actors, Victor McLaglen is on hand to play a bartender and Raft's pal. His character, frankly, is a bit hard to understand. Who his is and why he's there is pretty vague. Fortunately, this all becomes clear at the end--and it is a nifty one--making up for the general blandness of the rest of the film. The film has a few nice twists but also gives Raft a mostly passive sort of role for the leading man--and not a film that would help him regain his past prestige on the screen.