I like Justin Timberlake. As clumsy a tact as that may be to start a dialogue, it seems a necessary one in this particular, awkward case. Long derided as the pretty, white face of cultural vampirism, if nothing else, Timberlake used to make it look cool. There's no real need to go through his bonafides, but, hey: 'Cry Me a River' turned the now ancient Britney drama into gold, 'My Love' coincided with the rise of T.I. the pop star, the list goes on and on, and all along the way, Timberlake's career provided not one, but several, resurgences for national treasure Timbaland. Appropriation be damned, Futuresex and the first 20/20 Experience had *joints*.

His latest album, portrayed dramatically as a grand return – as well as some ambiguous, imagined “return to his roots” (sigh) – Man of the Woods, could more accurately be titled 'What Happened?: The Album'.

Playing like an early onset midlife crisis, in truth, Woods makes a sad sort of sense. In the 4+ years since the forced second 20/20 chapter, much of what allowed Timberlake to straddle musical, cultural, and racial realms has changed. The Buzzfeed era is much less forgiving of his antics, and a large chunk of his white audience is doubtlessly lost in Red Hat wearing delusion. It didn't hurt that Timberlake had a country pop influenced hit in 'Drink You Away' – leaning into his whiteness just made sense.

Did it have to be so clumsily executed? The teaser for the album felt as if Timberlake had gone far too into the role when he parodied Bon Iver on SNL, as he roamed forests and various dramatic landscapes. The former N'SYNC heartthrob may well feel a genuine connection to his Southern roots, but suddenly making it the focal point of his entire persona? For a man who's spent a career donned in suits dancing in shiny rooms, it's tough to swallow.

No less, he goes about it with the subtlety and grace of a Transformers writer's room, from the groan-worthy album title, to that teaser, to the songs found here. 'Flannel'? There's simply no way Timberlake has ever been in a position to necessitate 'Livin' Off the Land'.

The man himself seems, if not troubled by the sudden alteration, completely unsure of how to go about it. Lead single 'Filthy' was an early warning sign, not so much a song as a collection of limp catchphrases. “This ain't the clean version,” Timberlake tiredly insisted, while saying little else. Attempted recovery single no. 2, 'Supplies', suffers from the opposite problem. It's desperately overstuffed with clickbait jargon in an effort to paint the singer as conscious of world peril. As, dare we say, “woke”. We remember how you did Janet, Justin, we're not buying it.

Naturally, an album entirely helmed between sonic masters The Neptunes and Timbaland isn't going to be without some nice sounds. 'Midnight Summer Jam' boasts a catchy backdrop, and Alicia Keys helps breathe life into the effortless groove of 'Morning Light', but by and large, the production here is surprisingly staid and unsure of itself. It doesn't help that the album greatly overextends itself across more than an hour. Despite the album's presentation, the attempt to cash in on that Country good will is consciously on the back burner; there are flourishes and Timberlake occasionally forces a slight drawl, but his closest swings fall flat.

He may have offered a moment with Chris Stapleton at the Country Music Awards, but when the two reunite here for 'Say Something', it's for an unfortunately limp ballad that seems to extol the virtues of turning a blind eye. When they had such a massive platform to say, well, anything it's a shame they chose to proffer nothing. Naturally, Timberlake completely contradicts this message of non-statements on closing track 'Young Man', advising his son that he must always "stand for something". Apparently, Timberlake doesn't feel obligated to do the same for his audience. Meanwhile, wife Jessica Biel is given full interludes before and after 'Flannel', here to forcibly remind us all that Timberlake does indeed “make [her] feel sexy.” Lost some confidence there, Justin?

It's understandable if he has. The climate Justin Timberlake exists in may have changed, but did a course correction really require a pivot as grand as Man of the Woods? He surely could have offered some mea culpas, actually acknowledged his place as a white man who truly loves the spaces he works within, and more or less stuck to the same – successful, enjoyable – formula. So, perhaps this is truly the move the artist felt compelled to make, however opportunistic its timing appears. “Haters gonna say it's fake,” Timberlake frankly asserts on, 'Filthy'. They needn't even bother. Genuine or not, it simply doesn't work.