This is a generous-spirited and elegantly made, but not entirely persuasive, documentary that wants to open up the legacy of Jack Kerouac’s On the Road by making it relevant for younger generations, while still acknowledging how problematic and dated it is. In a way, that self-cancelling, internal contradiction is true to the spirit of the 1957 book itself: a work that alternates between passages of beauty and purple pulp, profound insight and dim-witted idiocy tied to the times in which it was written, especially when it comes to race and women.

Director Ebs Burnough and his starry lineup of interviewees valiantly try to outline those complexities with honesty, and the film is at its best when it homes in on the literary criticism – bringing in articulate readers of the text such as novelist Jay McInerney, who details the effort that went into making it look thrown together in a matter of weeks. Musician Natalie Merchant, meanwhile, thoughtfully unpacks what still resonates in the book, even though she confesses that, despite her best efforts, her own daughters haven’t been able to get through more than a few pages. Elsewhere, comedian-journalist W Kamau Bell, an unstoppable quote machine himself, wryly analyses the book’s blindspots on race, and has a great fantasy about what a fine road movie it would have been if Kerouac had gone travelling with James Baldwin. And, of course, Kerouac’s lover Joyce Johnson – a significant writer in her own right – recounts some choice, if familiar, anecdotes about her times with the author. The contributions from actors Josh Brolin and Matt Dillon, while sincere, are less striking.

What really doesn’t work, and feels like something tacked on at the misguided behest of a studio executive determined to make this all relevant, are the passages about Americans today, taking to the road for various reasons. There’s a woman driving to see her father, with whom she had a very difficult relationship, and reflecting on her life as a queer person; a couple who seem rather mismatched politically but are clearly quite in love, and who like to wander the country as an escape from traditional roles; and a family seeing one of their older sons going off to college. They’re all likable enough people, but the relationship to Kerouac and his work is tenous and flimsy.

• Kerouac’s Road: The Beat of a Nation is on digital platforms from 13 October.