Tangled has always had a bit of a mixed reputation. Although cinema-going audiences treated it fairly kindly, it struggled to make back its mammoth budget. Critics shrugged at it – complaining it was a little weak for the 50th Walt Disney Animated Classic (as if anyone remembers which number their favourite is). There was also a healthy dose of industry gossip around its marketing. It didn’t go out under the name Rapunzel, reportedly making the shift to a more neutral name to avoid putting boys off with a princessy label. The filmmakers defended the choice because of Flynn Rider, who they argued was a main character. Some dismissed this as marketing spin. Maybe so; it also happens to be true.

To understand how Flynn drove the final nail into the cookie-cutter prince coffin, let’s go back to Walt’s heyday. The prince template is pretty simple: he turns up, interrupts the princess to sing about love, possibly does some slaying or kissing (or both), marries the girl, and is promptly forgotten about. There’s a reason Maleficent got an origin story over Prince Philip – and she doesn’t even have a song. 

Snow White Prince (1)

Courtesy of: Walt Disney Pictures

Then, for a long time, there is no prince. There are cats (Thomas O’Malley, Oliver), dogs (Tramp, Pongo), little boys (Mowgli, Peter Pan) and even a fox who still makes the internet uncomfortably thirsty. Finally, Disney finds its own crown prince, the only man who’s spoken of in terms as hallowed as those reserved for Walt himself: Howard Ashman.

In Ashman’s short tenure, together with long-time musical partner Alan Menken, he helps spearhead a renaissance in Disney animation, which rescues the artists from the literal outbuilding they’ve been relegated to. A hugely talented lyricist and driven perfectionist, Ashman completes work on just two and a bit films before AIDS-related illness takes him prematurely. One of them, Beauty and the Beast, nets the first Best Film Oscar nomination for an animated feature and cracks open the Disney prince mold. After the Beast – erroneously but widely also known as Prince Adam – the pattern is fractured, dismantled. The prince is now an active character with his own history – a form that ultimately hits its peak when a smouldering swashbuckler teams up with a young woman nursing a chronic shampoo problem.

Beast

Courtesy of: Walt Disney Pictures

Counting as a prince anyone who has a corresponding official Disney Princess, the next few leading men are Aladdin, John Smith, Li Shang, and Naveen. For the first time, thanks to Ashman’s influence, male leads are getting ‘I want’ songs. Aladdin still has shades of a more sanitized matinee idol, but he’s also chatty, witty – and a criminal. We’ll skip over the white colonialist voiced by an alleged anti-semite misogynist (who also happens to be a character so boring a greedy pug out-performs him). Li Shang frustratingly has a white man’s singing voice, but a hell of a banger to belt out. And Naveen finally gets to full-on lean into comedy – “it’s not slime, it’s mucus” – though he’s a tad one dimensional, and overshadowed by justified indignation around his ambiguous ethnicity. And then there’s Flynn.

We probably have Dreamworks, among others, to thank for Flynn’s transition from farm boy on paper to dashing thief on screen. A string of edgier, funnier movies like the Shrek and Madagascar franchises were winning over audiences in a way Disney’s post-renaissance mixed bag wasn’t always managing. With slam-dunk casting in Zachary Levi, who brought to bear all his sexy nerd cred from the likes of Chuck, Flynn finally got to realise the blueprint laid out by Aladdin in full – without being the solo headline character. 

Flynn Rider Smoulder

Courtesy of: Walt Disney Pictures

A deeply reluctant hero, reliably unreliable and even riding under a fake name, the man who turns out to be Eugene Fitzherbert is painted with a dozen little details Cinderella and Snow White’s princes would’ve killed for. He opens the narrative – “this is the story of how I died” – although he quickly concedes it’s not really about him. He gets enough of a broadly-drawn back story that we begin to understand his motivations. His ongoing battle-slash-buddy-act with Maximus the horse (and to some extent Pascal the chameleon) plays with silent film flair. His reticence to join the tavern singalong in I’ve Got A Dream – only to tapdance his way through it as soon as he’s threatened – likewise has shades of early comedies and musicals. He derives his name from Errol, of course, but his emotional growth as a character doesn’t just come from falling in love with Rapunzel, but from learning from her; she rescues him, swinging from her magical tresses, and he borrows the frying pan she knocked him out with to fight, gleefully exclaiming “Oh mama, I have got to get me one of these!”. 

If the Beast was tamed by Belle’s gentleness, Aladdin plopped back on the straight and narrow (ish) by Jasmine’s status and Li Shang and Naveen learned to shine in the shade of a more accomplished partner, Flynn’s personality stays intact even after love. To the end, he’s still cracking jokes and playing up his self-centred act. And after Flynn, Disney’s bar for princes was set at full partnership level; without him, it’s hard to see how we would have got two-faced Hans and reindeer-scented Kristoff in Frozen, which decided to smash a few more princess tropes while it was at it.

Indeed, in the ten years since Tangled’s release, Frozen has been the only Walt Disney Animation Studios film, now franchise, to bother with the traditional monarchy set up at all. (One Pixar princess, Merida from Brave, has joined the official list; she has no prince.) The excellent Wreck-It Ralph gives it a comic nod at the end – and then plays with the princess brand in its somewhat less brilliant sequel. Moana’s Maui cracks jokes about being a chief’s daughter and having animal sidekicks. Big Hero 6 tackles the everyday heroism of grief and Zootopia goes straight in on racism. Still, all things are circular, so it’s likely Disney will come back to the cartoon bad boy with a heart of gold at some point. And when they do, they’ll have their work cut out for them to nail one better than they did Flynn Rider.