Justin Timberlake's career has been painstakingly built and sustained on a search for a very conventional authenticity. From the minute he parachuted out of boy band *NSYNC and into a solo career launched by turn-of-the-century production geniuses Timbaland and The Neptunes, Timberlake has been keen that the world should take him seriously. "I just didn't know any better," he scoffed about his teen-pop years in a <em>Rolling Stone</em> interview in 2003 – one that was straplined: "The singer earns some cred, trading his teen beats for R&B swagger." It is a well-worn path towards music industry adulthood, but it is perhaps a little surprising that Timberlake is still preoccupied with it. The 37-year-old opens his fifth solo album, <em>Man of the Woods</em>, by reiterating his credibility with a thud. "Haters gonna say it's fake/So real," he yelps over warmed-up warped funk that would have sounded compellingly weird in 2006, when Timberlake released <em>FutureSex/LoveSounds</em>, his most ambitious magnum opus. Not that futuristic innovation is the kind of cred he seeks these days. Rather, <em>Man of the Woods</em> finally makes the subtext of Timberlake's career explicit in eliding authenticity and masculinity. It turns out that an adolescence as a fluffy-headed boy band moppet regularly impugned on record by Eminem wasn't just wounding as a musician, but as a man, and he is still trying to correct that image by any and all means necessary. <em>On Man of the Woods</em>, that means trying to square Timberlake's past and present, his youth and his middle age, by trying to have his cake of disparate masculine archetypes and eat it. Pre-release teasers – the title, the cover photo depicting Timberlake gazing seriously over isolated Midwest countryside, his horses grazing behind him – seemed to reinvent him as a rugged frontiersman. In terms of chart trends, it is the latest in a line of mainstream pop stars (Lady Gaga, Miley Cyrus) discovering their country roots a few years into their career, accompanied by a nifty PR line about how this has made for their most "personal" (in other words, authentic) album yet. It is a particular sort of aesthetic volte-face that begs the question of how disposable their dalliances in other genres – specifically, the R&B and rap cultures that Timberlake and Cyrus built their "cool" on – were in the first place. Sonically, though, Timberlake has hedged his bets, with the first half of Man of the Woods sticking to lite-funk with a cheesy entertainer’s grin, before it takes a country turn that mostly means sentimental domestic balladry. Indeed, it is territory he has dabbled in before. When Timbaland first tried to pioneer a country-rap/R&B blend he called “hick-hop” in the mid-2000s, to artistically brilliant but commercially unsuccessful effect, Timberlake was right there with him, guesting on Bubba Sparxxx’s 2003 album Deliverance and sampled on Sparxxx and Kiley Dean’s lost gem Nowhere. A few years later, one of Timberlake’s best singles, What Goes Around… Comes Around, fused a bluegrass twang with electronic soul. Here, though, the sounds are mostly segregated, with the bass-heavy bluegrass-meets-trap of Supplies a commendable exception. What is more interesting is how the plaid-shirted, down-home Southern dad-bro character of the album’s back half feels of a piece with the suave, betuxed seducer who leads off – and, for that matter, with the turtleneck-wearing tech whizz Timberlake plays in the video for lead single Filthy. On <em>Man of the Woods</em>, a real man is somebody who can do both. A real man is wealthy, with a veneer of sophistication, as evidenced by the expensive-sounding beats on tracks such as Midnight Summer Jam, a Bruno Mars-style cornfest that comes on like the soundtrack to a <em>Big Little Lies</em> fund-raiser (or perhaps, when a generically sultry female voice starts whispering in your ear, more like the Presidents Club). A real man has a work ethic (for Timberlake, this means doing his utmost to impersonate a manual labourer on<em> Livin' Off The Land</em>. A real man probably watches <em>The Walking Dead</em>, that televisual ode to real men and their brute force, which Timberlake carefully references on <em>Supplies</em>. A real man is a dad – more than that, a paterfamilias passing on homespun wisdom to his son, as Timberlake does on two unlistenably mawkish cuts that close the album. A real man gets the girl, too. Timberlake's decade-plus staircase to credibility has also used the bodies of women as crucial rungs: <em>Cry Me a River</em>, his first critical crossover hit and a song he and Timbaland seem to have spent a decade-and-a-half rewriting, spun a mean-spirited revenge narrative from the ashes of Timberlake's relationship with Britney Spears. Fourteen years ago, his Superbowl performance with Janet Jackson gave the world the phrase "wardrobe malfunction" amid confected moral outrage that torpedoed the latter R&B legend's career – but which Timberlake himself carefully sidestepped. By contrast, 14 years later, Timberlake's return to the Super Bowl this week was a determinedly chaste affair, short on thrills of any kind. A succession of hits were blunted and de-eroticised by a dress code for the singer and his dancers of any old tat from the Urban Outfitters' bargain basement paired with an attention-deficit medley format, which rarely fails to feel like a performer is pressing the panic button midway through a song to keep an audience from wandering away. And even so, Timberlake demonstrated how little he had learnt from the Jackson experience by duetting, midway through, with a gargantuan projection of Prince for a cover of <em>I Would Die 4 U</em> – a technological exhumation that, it had become apparent in the week preceding the Super Bowl, had been very much against Prince's own wishes. From using the body of a black woman at her expense to bolster a white man's image to using the body of a dead black man for much the same reason – it is not exactly progress. It can be no surprise, then, that women exist only as trophies on <em>Man of the Woods</em>. The premier trophy is Timberlake's wife, Jessica Biel, who is permitted a voice to massage her husband's ego on a knuckle-gnawingly awkward interlude <em>Hers</em>. Repeatedly, the highest compliment Timberlake pays the object of his affection is that he brags about her. "I'm sorry, baby… it's my pride," he shrugs on the title track – a real man has manly pride – before lurching into even more dubious territory, leering: "Tonight, if I take it too far, that's OK… I hear the making up's fun." In some ways, Timberlake is a victim of the rapidly changing zeitgeist – though surely it is a pop star’s job to have their finger on its pulse, if not actually create it. His aspirational masculinity is the same story he has been peddling for his whole career – and when he and his collaborators were young and fresh, it resulted in genius. It is also the narrative that pop culture as a whole has sold us for a good half-century – which is why it is increasingly feeling so familiar and so tiresome. Even boring conventional men can be attractive sometimes, which is why the lush, drifting Montana is a highlight, and the beats exploding like piñatas on <em>Midnight Summer Jam </em>are a satisfying touch. But there are younger artists exploring masculinity in far more sophisticated ways these days: it is hard to listen to Timberlake trying to create a tropical-resort vibe on <em>Wave</em> without wondering what an artist such as Miguel, for example, could do with the song's mood. 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