In the chilly new neo-noir The Burnt Orange Heresy, Mick Jagger plays Joseph Cassidy, a conniving art dealer who manipulates a desperate art critic into procuring, by whatever means necessary, a painting from a reclusive master working under his patronage. Aside from two blink-and-you’ll-miss-it cameos between 2007 and 2008 (in the short-lived comedy series The Knights of Prosperity and the Jason Statham crime caper The Bank Job, respectively) and one Saturday Night Live hosting gig in 2012, this marks the 77-year-old star’s first substantial acting job in almost 20 years. It’s a welcome, if seemingly left-field return for the rock legend. But then, his long and sporadic acting career has always been a bit left-field, both in his choice of roles and the quality of his performances.

No one would accuse Jagger of being a great actor – as far as the rock stars of his generation to make the jump to screen he’s neither the best (that would be David Bowie, Kris Kristofferson or Tom Waits) nor the worst (that would be Bob Dylan or, god help us, Neil Diamond). He has, however, delivered at least one truly great performance in one truly great movie, as well as several very interesting ones.

Jagger has been a staple of cinema since the late ’60s, when he first collaborated with the likes of Jean-Luc Godard and Kenneth Anger on avant garde experimental films. He and his fellow Rolling Stones were front and center in Albert and David Maysles’ masterful documentary Gimme Shelter, about the disastrous Altamont Free Concert of 1969. (Is there a better visual representation in all of cinema for the death of the ’60s than the exhausted, ambiguous look on Jagger’s face during the closing moments of that film?) Like his aforementioned musical contemporaries, Jagger was quick to use his stardom to get into acting proper, starting with two back-to-back starring roles in 1970.

The first of these came in Donald Cammell and Nicolas Roeg’s Performance, a darkly surreal and graphically erotic story about subsumed identity, individual alienation and sexual ambiguity set within London’s criminal counter cultural underworld. Jagger, who doesn’t show up until an hour into the film, plays Turner, a reclusive, strung-out rock star wiling away his days in a rundown Notting Hill townhouse alongside two female lovers (one of them played by Keith Richards’ then partner, Anita Pallenberg, resulting in much behind-the-scenes drama).

Jagger’s performance in Performance feels completely natural, so much so that there seems to be hardly any daylight between Turner and himself. While it’s easy to assume this was simply the result of his playing a slightly-fictionalized version of himself, those involved claim otherwise: by all accounts, Jagger was a dedicated and hard-working professional, one whose work ethic and attitude were worlds apart from his character’s.

Jagger believed in the film, which was more than could be said of its producers at Warner Brothers, who thought they were getting a hip comic romp in the vein of a Hard Day’s Night, rather than the high art, Bergman-on-psilocybin film that Cammell and Roeg delivered. So baffled and horrified were they that they shelved it for over a year, quietly releasing a re-edited version in a handful of theaters in England and the US. Its release was met with equal disdain from critics, with the reviewer for the New York Times writing: “You do not have to be a drug addict, pederast, sadomasochist or nitwit to enjoy Performance, but being one or more of those things would help.”

Mick Jagger in Ned Kelly. Photograph: Allstar/WOOD

But vindication lay in store for Performance, as it would go on to earn status as a cult favorite before ultimately being recognized one of the best and most influential films of its era. Among the film’s loudest proselytizers is Martin Scorsese, whose visceral, psychologically complex gangster movies are clearly indebted to it. Scorsese – who has used the music of the Rolling Stones in a number of his films, directed the band’s 2008 concert film Shine a Light and co-produced the HBO rock drama Vinyl alongside Jagger – pays direct homage to Performance in Goodfellas, playing its centerpiece musical number, Memo from Turner, in the background of a pivotal scene. By 2009, the rest of the film scene had caught up with Scorsese, with Jagger’s turn in Performance landing at the top of Film Comment’s poll of the best acting performances by a musical performer.

Alas, no such vindication lay in store for Jagger’s other film from that same year, Ned Kelly. Directed by Tony Richardson, the turgid biopic of the Australian bushranger and folk hero tried to do for its titular outlaw what Bonnie & Clyde had done for theirs three years prior, only to fail spectacularly. The film was doomed from the start: Jagger’s casting (he replaced original leading man Ian McKellen at the behest of the studio) was met with immediate backlash due to his lack of resemblance to the real Kelly, as well his lack of Australian and Irish roots. Shortly before filming was set to begin, founding Stones member Brian Jones was fired from the band and less than a month later, he drowned in his swimming pool. Jagger and his girlfriend at the time, the singer and actor Marianne Faithfull, who was set to co-star alongside him in Kelly, were contractually obligated to be in Australia for filming and missed Jones’s funeral. Their relationship already in free fall, Faithfull attempted suicide soon thereafter by taking an overdose of pills and ended up in a coma. She came out of it but had to be replaced in the movie. Even more injury lay in store, with Jagger suffering a painful and debilitating injury during the filming of a climactic shootout after a prop gun backfired a loaded blank into his hand.

By the time Ned Kelly was completed, Jagger had publicly disowned it, later referring to it as “shit”. Even accounting for personal baggage, he’s not wrong: a painfully dull film in and of itself, it’s further hampered by his truly terrible lead performance. Jagger intended to use the experience to “focus on being a character actor”, but gone is any hint of the naturalism or dark charisma he showcased in his previous role. Instead, he gives a wooden and braying performance, one made unintentionally hilarious by his ridiculous Amish-style beard and awful and inconsistent Irish brogue.

Given the rotten reception that met Performance and Ned Kelly, you couldn’t have blamed Jagger if he’d called it quits as a thespian and focused solely on music. Yet, by the end of the decade he was ready to give acting another go. He started off smaller this time, making short appearances in British TV movies The War Between the Tates and The Rutles: All You Need is Cash (in which he’s clearly having a blast taking the piss out of himself and the Beatles), as well as an obscure short about the French dramatist Antonin Artaud.

Jagger was primed to make a big return to international cinema with his next film project, co-starring alongside Jason Robards in Werner Herzog’s adventure epic Fitzcarraldo. He was to play Wilbur, a “simple-minded actor” who accompanies Robards’ mad dreamer in his quest to drag a steamship over a mountain in the Amazon basin. The production completed several weeks of filming when Robards caught dysentery and had to quit. With the production put on hold for six weeks, Jagger’s commitments to the recording of a new Stones album forced him to likewise drop out.

Herzog has described Jagger’s exit as “the biggest loss … in my career”, and rather than recast, he cut the character out of the film altogether. Against all odds, Herzog would go on to complete Fitzcarraldo, and while the film ranks as one of his best, one can’t help but wonder what might have been. The brief but intriguing footage of Jagger and Robards shown in the documentaries Burden of Dreams and My Best Fiend suggest something truly special, and if all had gone according to the original plan, Jagger may well have matched or even eclipsed his work in Performance. Similarly, one wonders what might have been had he won the role of Frank-N-Furter in Rocky Horror Picture Show, for which he auditioned, or if Argentinian madman Alejandro Jodorowsky been able to bring his wildly ambitious adaptation of the sci-fi epic Dune – in which Jagger had agreed to play the lead villain – to fruition.

After signing on to yet another aborted project (an adaptation of Vladimir Nabokov’s Laughter in the Dark) and making a bizarre appearance on a single episode of Shelley Duvall’s children’s program Faerie Tale Theater (in which he’s transformed into a Chinese emperor with the help of some … unfortunate … makeup), Jagger gave his only substantial performance of the 80s in director Julien Temple’s satirical adventure film Running Out of Luck, where he plays a heightened version of himself lost in Brazil. Jagger claims to have turned down dozens of rock star roles over the years, so it’s a wonder what he saw in this one. While the film attempts to be a self-deprecating send-up of celebrity culture and western materialism, it comes off as a garish vanity project, as well as an expensive personal vacation paid for by the studio’s dime.

In 1992, Jagger showed up in what is probably his most widely seen film, the corny, but surprisingly prescient sci-fi action thriller Freejack. As ruthless future bounty hunter – or “bonejacker” – Victor Vacendak, Jagger is basically playing a stone-faced Elmer Fudd to Emilio Estevez’s very confused Bugs Bunny, as he chases him through a dystopian New York City in the far-off year of 2009. Despite the grimace Jagger wears throughout he’s clearly having a blast. It’s a bizarre performance in a very silly movie, but one that makes for a relentlessly entertaining watch, thanks in large part to his efforts.

After a five-year hiatus, Jagger returned to the screen in Bent, the harrowing adaptation of Martin Sherman’s queer Holocaust drama, where he played a ringleader for Berlin’s gay underground (and an informant to the Gestapo) in the days leading up to The Night of the Long Knives. Jagger spends much of his short screen time dressed in drag and while it’s not exactly surprising to see him in such a role – he has long used his image to toy with societal standards of gender and sexuality, after all – his air of faded glamour and his haunted visage lingers even amongst the brutality of the rest of the film.

Donald Sutherland, Mick Jagger, Elizabeth Debicki and Claes Bang in The Burnt Orange Heresy Photograph: Sony Pictures Classics

His next role – and the last substantial one he would take until The Burnt Orange Heresy – came in The Man from Elysian Fields. Directed by George Hickenlooper (who co-directed the documentary Being Mick that same year), it’s one of the worst movies Jagger has appeared in, although it contains one of his best performances. The laughably convoluted and improbable plot revolves around an unbearably entitled struggling novelist (Andy Garcia) becoming a male escort in order to support his family. The whole thing plays out like a slightly more expensive, but much less erotic, feature-length episode of the Red Shoe Diaries, thanks in no small part to Jagger’s omnipresent narration. That said, Jagger’s sensitive, wounded performance as an ageing and heartbroken gigolo reckoning with a life of loneliness and wasted potential is surprisingly effective, so much so that one has to assume he dug deep into his own history of promiscuity and heartbreak.

Between his work in Bent and The Man from Elysian Fields, it seems clear that Jagger’s true calling in acting should have seen him playing morally tortured supporting roles in noirs and melodramas, but alas, he missed that boat by a few too many decades. Still, his fun, seedy turn in The Burnt Orange Heresy shows that he still has some good parts left in him, although whether it suggests a renewed interest in acting remains to be seen (especially since he continues to grind it out at his day job).