Nostalgia is a funny thing. Like many film fans, my list of all-time favorites includes a few suspect items that take a little more justification than the undisputed classics. Would I have enjoyed Labyrinth as much if I’d first seen it as an adult? Would I have as much affection for Frank Coraci’s Around the World in 80 Days and its baffling cast if I hadn’t been brutally hungover the first time I saw it, allowing its blunt emotional message (“Friendship is Actually Good”) to reduce me to a blubbering mess? There’s literally no way of knowing. 

Summer Rental is another film I find it hard to justify my love for. It’s a mid-level 80s comedy starring John Candy as Jack Chester, a stressed-out air traffic controller who has a National Lampoon-adjacent misadventure on a Florida vacation. Here’s the thing though – I first saw Summer Rental in 2014. Can nostalgia still be a valid excuse for loving a film that I saw nearly 30 years after its initial release? To some extent, I think it can – this film is formulaic enough that a good amount of the good-hearted familiarity I felt towards it probably leaked out of other, similar films. It’s also so proudly, defiantly a product of the mid-1980s: more than one Walkman-esque portable listening device appears, along with a prominent Casiotone keyboard, and is if that weren’t enough, two teenagers delight in the theme tune from Footloose while also walking past a poster for Footloose! You can almost smell the Kevin Bacon.

It’s not just the ‘80s trimmings either – no disrespect to Candy, he frequently played very similar characters, so it doesn’t take much effort to slip into their world. Director Carl Reiner also followed this film with another summer comedy, Summer School, which actually was a staple of my childhood. But even so, it seems slightly odd that I found myself powerless to resist two rewatches of Summer Rental in the weeks that followed my initial discovery; first to show off its lovably dated charms to my girlfriend, and then to break in a new Netflix subscription with an “old favourite” that I’d loved for all of… a couple of months. Had the cool, relaxed vibes of Jimmy Buffett’s timeless “Turning Around” broken me forever? Or had I simply developed a perfectly natural obsession with the scene, late in the film, where Candy’s youngest daughter is obviously dubbed by an adult for one glorious line of dialogue? Three years on from this strange “Summer of Summer Rental”, I am none the wiser.

The film opens with a window into Jack Chester’s working day. Denied coffee by his concerned wife (“it gives you heartburn!”) and presented with an uncooked egg by his literal-minded daughter, he finds himself sipping herbal tea, covered in raw yolk, and stuck in traffic. After thirteen years of uninterrupted service at his job, a few low-key disasters lead to an enforced vacation – quite why he is so reluctant to take time away from work is never really explained – where he is free to inflict his personal brand of well-intentioned chaos on a whole new world. Sunburn, frisbee-related slapstick and a boat-related injury quickly ensue. But, just as Summer Rental seems like it might get stuck in a rut, it makes an unexpected shift into underdog sports movie territory.

While this film predates The Simpsons, it’s hard not to see Jack Chester as a Homer Simpson type. Frequently obnoxious and incompetent to “walking disaster” levels, he nevertheless makes friends wherever he goes. A catastrophic trip to the local seafood restaurant early in the film leads the Chester family to seek refuge at a run-down eatery run by Scully, a retired pirate played by the ever-welcome Rip Torn. Jack and Scully soon become inseparable, and after a drunken conversation  that includes such delights as an argument over whether James Cagney could beat Sylvester Stallone in a fight,  a plot is hatched. Can Scully train Jack to be a sailor? In classic ‘80s movie fashion, probably!

Jack and Scully find their perfect adversary in Al Pellet, a local snob who wins the town’s regatta every year and, due to the charming whims of the comedy screenplay, the source of every single one of Jack’s frustrations. In another casting masterstroke, Pellet is played to villainous perfection by Richard Crenna; his despicable wealth and success (Boo! Hiss!!) bring Jack’s everyman qualities into sharp relief and before long the whole family is back on board, working together in joyous montage to bring Pellet down and secure a feel-good victory for the ages.

It’s with casting like Torn and Crenna that Summer Rental continues to find aces up its sleeve. Candy’s oldest child is played by Kerri Green, fresh from The Goonies (which has its own nostalgia-vs-quality issues) and soon to star alongside Corey Haim in 1986’s Lucas (a genuine, underrated masterpiece of the coming-of-age genre that I’d be writing about now if it had come out a few months earlier.) Alan Silvestri’s score, packed with steel drums, also elevates proceedings – a summer movie score that just drips sunshine, with dynamic action themes that even manage to make sailing seem exciting (a feat that should probably have won some kind of special Oscar). The script may rely on sudden changes of heart and sketchy motivations, but it’s also funny, and in a beguilingly strange way – plenty of “who is this film actually meant for?” adult humour is crammed into its family-friendly framework, and running jokes range from a neighbour who can’t stop showing off her breast implants to an exceedingly Scottish sailor who Scully repeatedly refers to, inexplicably, as a “dumb Swede”. It’s not smart, but it never feels lazy.

It’s hard to know if this is actually a better-than-average comedy film, or if it just clicked with some dormant nostalgia in my brain. Rewatching it for this article, I actually enjoyed it every bit as much as I did back in the Summer of Summer Rental; Rip Torn especially deserves praise for a truly memorable performance, but it feels like everyone involved in the making of this film tried just a little bit harder than you might expect, and the end result glows with a strange summery magic because of it. I’m still unsure whether I can truly recommend it to other people, but I’m glad somebody recommended it to me – there are times in my life when I just need this kind of fluffy, heartwarming film, and I’m glad this one was there to cheer me up back in 2014.