Bob Hope, Bing Crosby, Dorothy Lamour and a big homoerotic elephant in the room star in this beginning of the famous Road series. It’s lame when young people laugh at old movies merely because they’re old, but there’s nothing wrong with acknowledging lines and moments from past films that have acquired new dimensions and unintentional double entendre over time. This is most true with comedies and even more so with a breezy, weightless fluffball such as Road to Singapore. As long as you’re laughing, you’re fine. That’s all this movie cares about.
So, let’s get into it: Hope and Crosby love each other so much here, this is nearly a gay romantic comedy. They sleep next to each other. They avoid women together. Bing Crosby wants to shirk his rich family to spend all day goofing off with his more lowdown buddy. That’s why those two crazy kids are in Singapore, getting into lots of good old-fashioned trouble and stepping on a few more retroactively queer asides (including a lesbian marriage joke). Hope is reliably funny and Crosby is reliably smooth, holds his own in the laughs department next to his co-star’s relentless ad-libbing and doesn’t seem at all like the kind of guy whose children would later write memoirs of what a nighmarishly abusive father he was.
This was among the biggest hits of 1940 and it spawned more films that aren’t so much sequels, as we know them today (they aren’t the further adventures of these same characters), but rather more flogging of the formula and 100% self-aware of it, often joking about it. If you like one of these movies, you’re probably going to like them all.