With his high pompadour and a penchant for boxy leather jackets and bold patterned shirts, Joaquim Calçada looks like he has wandered straight out of a 1970s movie. His face, though not conventionally handsome, has a kind of cinematic quality that could have promised a fruitful career as a tough-guy character actor in a bygone era before Instagramified prettiness took over film casting. Perhaps inspired by Calçada’s distinctive looks, Susana Nobre’s intriguing docufiction brings a playful dose of smoke and mirrors to a life story that is far from glamorous.

In fact, Calçada is an unemployed Portuguese man nearing retirement age, who earlier in his life spent two decades in the US as an undocumented immigrant. Now he is caught in a cruel predicament where he can only claim unemployment benefits by first proving that he has unsuccessfully applied for jobs elsewhere. This means visiting random places of business and manually collecting stamps from employers who confirm that he is unfit for work. Aside from this undignifying paper trail, the red tape merry-go-round sends Calçada back on a wistful journey to the past. Here is where reality and artifice magically fuse. Seated behind the steering wheel, he fondly recalls his time in New York, where he worked as a cabbie and a limo chauffeur. The camera then gradually pulls back to reveal a film set and the rear projection screen behind Calçada’s stationary car.

These stylised flourishes – which include a Scorsese-style sequence where Calçada acts out a confrontation between friends – lend a distinctive lyricism to experiences of hardship and loss that are, unfortunately, all too common. The warm glow of the 16mm film stock that Nobre uses further heightens this sense of cinematic romanticism. Though neglected by the system that should have helped him with a safety net, Calçada is still, for a moment, the star of his own movie.

• Jack’s Ride is available from 14 July on True Story.