Is Bob Dylan trolling us? His 36th studio album, Shadows in the Night, is a collection of old jazz crooner standards most closely associated with Frank Sinatra. It's an idea seemingly as weird as his phlegmy Christmas album or his leering Victoria's Secret ad. In the '60s, Sinatra was arguably for squares; entrenched in Vegas and disdainful of rock'n'roll (which he had called "the most brutal, ugly, desperate, vicious form of expression it has been my misfortune to hear"), he represented the establishment against which the counterculture was kicking, and that made him a kind of anti-Dylan. And then there's the fact that crooning is all about the voice—making it smooth yet expressive, agile yet graceful. Just as Dylan's songwriting exploded the notion of the tightly structured pop tune, his voice has roundly rejected the notion that pop singers must sound pretty.

While it may prompt some exasperated debates, Dylan has in fact been teasing this project for years, if not decades. A few of the songs on Shadows in the Night have appeared sporadically in his setlists since the 1990s, and in his 2004 memoir, Chronicles, Volume One, Dylan even professed his fandom for the Chairman of the Board, even if he subtly admitted that the crooner wasn't exactly a popular figure among the folkies in the Village: "When Frank sang ["Ebb Tide"], I could hear everything in his voice—death, God and the universe, everything. I had other things to do, though, and I couldn't be listening to that stuff much."

In other words, Shadows in the Night represents a lifelong appreciation for Sinatra, but more than that, Dylan is toasting a very specific era in pop songwriting. He's not interested in aping the man's vocal style (which would be laughable) or retreading his signature tunes (which would be redundant). There's no "Strangers in the Night" or "My Way" on here, nor is there a single dooby-dooby-doo. Instead, Dylan digs deep, picking personal favorites rather than obvious hits. "Some Enchanted Evening" and "That Lucky Old Sun" may be familiar to many listeners, but others, like "Stay With Me" and "Where Are You?" are more obscure, which allows Dylan to put his stamp on them without sounding like he's falling back on that late-career cliché: the standards album.

Rather than mimic the robust orchestral arrangements that define Sinatra's catalog, Dylan strips these songs down considerably. According to a statement on his website, he's not covering them, but "uncovering" them: "Lifting them out of the grave and bringing them into the light of day." There are some gentle horn charts on "The Night We Called It a Day", but they're generally unobtrusive, included less for dramatic effect and more for simple ambience. His small band accompanies him sensitively and sympathetically, often playing so quietly that it sounds like Dylan is singing a cappella. The lead instrument here is Donny Herron's pedal steel, which is so crucial to the album's moonlit ambience that it might as well hang the stars from the night sky.

And what do you know, Dylan can actually sing. Without sounding overly reverent, he croons persuasively, especially on "Why Try to Change Me Now". That song, recorded by Sinatra in 1959 for his album No One Cares, resonates powerfully on Shadows in the Night, with a performance so assured you might think Dylan wrote it himself. And perhaps that's why Dylan gravitates to these tunes. Never the most confessional songwriter—he dodges more than he professes—he has remained guarded about his inner life, making him both the most studied songwriter of the rock era and also the least known. But "Why Try to Change Me Now" may be one of the most revealing tunes he has sung in the twentieth century, allowing him to settle into the role of the lovable curmudgeon, a man who understands he's a mess but is too old to change. It's the best reason he's given for recording this album.

Because these songs seemingly reveal some new facets of Dylan's character and celebrity, they comprise a fascinating and conceptually rich object whose meaning will be debated and dissected for years to come. In particular Shadows in the Night asks us to hear these crooner anthems as folk tunes, as though Sinatra was Seeger with a tux and a stint at the Sands. While ignoring social or political dilemmas, they speak to certain emotional conundrums common to everyone: how to live with love and heartbreak, how to survive on whimsy and regret. Trying to explain the nature of attraction on "Some Enchanted Evening", Dylan offers a sly wink as he sings, "Fools offer reasons, wise men never try