Halfway through his Vineyard vacation, Obama staffers tweeted his second annual, and last ever, presidential playlist.

Like last year's set, this slate of seasonal jams has a spunky side one for daytime and a sultrier side two for nighttime. But this new mix skews more contemporary, with fewer generic oldies, and, in its modern moodiness, seems not so combed over. It's even possible we've been granted authentic witness to the president's raw coolness, and his attitudes about leaving office.

The first track, "LoveHate Thing" by Washington, D.C.'s Wale, lays out his bipolar embrace of the highest office in the land—that mixture of disdain for service and love of its perks. Other daytime tracks, "Home," "Smooth Sailin'," "Many the Miles," "So Ambitious," "As We Enter," "Forever Begins," and "Don't Owe You a Thang," flow together to reflect the same: While this president has enjoyed his reign, when he shrugs off the ermine robe of the burdensome office, he'll welcome the sweet relief of a new lightness, and, indeed, he won't owe us a thang. But, as the Times profile showed, somber reflection and surely some regret, too, will seep in when the sun goes down. Fittingly, the afterhours set takes on a more confessional feel with "If I Have My Way," "So Very Hard To Go," and "I Get Lonely" folded in amid a selection of summery love songs.

Bearing in mind executive isolation and this executive's mercurial regard for the office he'll be leaving, his transition back to civilian life could well up some pretty complicated feelings. So, to help him ease into that purgatorial phase and face the limits of his legacy, the following ten songs belong on "President Obama's 2016 Winter Playlist."

1. "Fame" - David Bowie

Near the end of a star-studded presidency, Obama has already begun to learn the hard way that, to paraphrase Oscar Wilde, the only thing worse than the constant scrutiny of a "splintered media" is not being scrutinized anymore. Bid a fond farewell to full-focus fame and her intoxicating wiles—she's brought you pretty far. As David Bowie tells us, "Fame makes man take things over."

2. "Ooh La La" - the Faces

The president's advice for his would-be successors back in December included a confession, "If you are interested just because you like the title or you like the trappings or you like the power or the fame or the celebrity, that side of it wears off pretty quick. At least it has for me." As if to say, anyone seeking the presidency ought to have a serious reason—at least, I wish I'd had one. In other words, he wished that he knew what he knows now when he was younger.

3. "Missed Opportunity" - Hall & Oates

Could Obama's most profound legacy end up being his failing to acknowledge the existential threat posed by Islamic terrorists and thereby irreparably damaging global security? Gee, that's a scary thought. In that vein, let's enjoy this eighties jam.

4. "Ol' 55" - Tom Waits

The president has just had a birthday. He's 55—just like the year of Tom Waits's Cadillac. Some read wistful nostalgia into this track from Closing Time, while Waits insists it's just a song about his car. President Obama, who's joked about his weathered looks, should enjoy the comparison to a beloved decades-old automobile.

5. "Community of Hope" - P.J. Harvey

This single from P.J. Harvey might just be playing on the ironic naming of a failed housing project plan. But it also contrasts the highly effective empty messaging of the Obama campaign with the unfulfilled "hopes" of the Obama era.

6. "Rehearsals for Retirement" - Phil Ochs

In this somber protest song, Ochs autopsied the American spirit. Governance by guilt and spiritually corrupt decadence seem to support his diagnosis of self-defeat. Happy retirement, Mr. President.

7. "Sophisticated Lady" - Billie Holiday

Sadness is inevitable in times of transition. As a Billie Holiday fan, the president should enjoy her lilting rendition of a popular standard. It's a perfect nighttime track to wallow with when he's feeling low.

8. "Don't Blame Me" - Nat King Cole

This lovey-dovey standard seems more the president's taste than "We Didn't Start the Fire." (There's a Trumpian flavor to that scrappy striver Billy Joel, anyway—at least in how he's flipped personal slights into McHits). But the message of inculpability is roughly the same.

9. "Solitude" - Duke Ellington

In just a few months, Mr. President, nobody will care how many almonds.

10. "Casey Jones" - the Grateful Dead

What's left to do but take a full-circle trip back through the habits of his freer years? Ride that train, sir.