Match the Obama playlist song to the intern who picked it

Did Obama really pick these jams?

Did Obama really pick these jams?

Cynicism: Conan O'Brien can't stand it; Jon Hamm thinks it hurts Mad Men fans; President Barack Obama is not a fan. Still, a healthy dose of cynicism is sometimes essential, lest we turn into the kind of gullible democracy — or oligarchy, depending on whom you ask — that makes a Clinton vs. Bush election the antithesis of Sophie's Choice in 2016. Cynicism is less essential when applied to music playlists, but forgive our raised eyebrows when Obama, mid-vacation on Martha's Vineyard, released his summertime Spotify mix last Friday.

Was Obama hunched over his laptop, headphones affixed, getting all Rob from High Fidelity instead of taking a much-needed breather from being leader of the free world? Maybe ... or maybe a fleet of White House interns was tasked with undertaking Operation Presidential Cool: Lame Duck Culture Cred Relatability Points. For fun, let's (cynically!) assume that's the case and match the (fictional!) White House intern to the cut he or she chose for "The President's Summer Playlist." 

OK, first, here's the official two-part playlist, as announced by the man himself. 
— President Obama (@POTUS) August 14, 2015 Day
1. The Temptations — "Ain't Too Proud to Beg"
2. The Isley Brothers — "Live It Up Pts 1 & 2"
3. Talib Kweli & Hi Tek — "Memories Live"
4. Bob Dylan — "Tombstone Blues"
5. Bob Marley & The Wailers — "So Much Trouble in the World"
6. Coldplay — "Paradise"
7. Howlin' Wolf — "Wang Dang Doodle"
8. Stevie Wonder — "Another Star"
9. Sly & the Family Stone — "Hot Fun in the Summertime"
10. Low Cut Connie — "Boozophilia"
11. Brandi Carlile — "Wherever Is Your Heart"
12. Nappy Roots — "Good Day"
13. John Legend and Andre 3000 — "Green Light"
14. The Rolling Stones — "Gimme Shelter"
15. Aretha Franklin — "Rock Steady" 
16. Okkervil River — "Down Down the Deep River"
17. Justin Timberlake — "Pusher Love Girl"
18. Florence + The Machine — "Shake It Out"
19. Sonora Carruseles — "La Salsa La Traigo Yo"

1. John Coltrane — "My Favorite Things"
2. Beyoncé featuring Frank Ocean — "Superpower" 
3. Van Morrison — "Moondance"
4. Lianne La Havas — "Is Your Love Big Enough?"
5. Al Green — "How Can You Mend a Broken Heart"
6. Aoife O’Donovan — "Red & White & Blue & Gold"
7. Lauryn Hill and D'Angelo — "Nothing Even Matters"
8. Frank Sinatra and Count Basie — "The Best Is Yet to Come"
9. Ray Charles — "You Don’t Know Me"
10. Mary J Blige and Raphael Saadiq — "I Found My Everything"
11. Joni Mitchell — "Help Me"
12. Otis Redding — "I’ve Got Dreams to Remember"
13. Leonard Cohen — "Suzanne"
14. Nina Simone — "Feeling Good"
15. The Lumineers — "Stubborn Love"
16. Cassandra Wilson — "Until"
17. Mos Def — "UMI Says"
18. Billie Holiday — "The Very Thought of You"
19. Miles Davis — "Flamenco Sketches"
20. Erykah Badu — "Woo"

And here is O's trusty team of music-savvy interns. Can you guess which 'tern picked which tune!? 

A. Jeff Winthrop: "We placed the president on Marc Maron's WTF podcast in June to leverage goodwill among minimally engaged, trend-setting millennials. This playlist needs some indie-rock flavor, but nothing that borders on the abrasive or obscene; the prez needs to appear as though he's aware the Mumfords have happened, and he's already chasing the next one. I better throw in exactly one nod to Latino voters, too." 
B. Rachel Mortenson: "Pop music the great unifier. Studies demonstrate that mainstream voter contingents seek to project their own unique identities through culturally identifiable memes. Barack may be the president, but he's still fun, as far as young Top 40 consumers need to know. Bonus demo: Moms and dads will smirk and say, 'I think Sasha and Malia got ahold of O's Macbook!' Of course, we'll have to avoid any blowout-spurring additions like Ariana Grande; she lost her presidential playlist privileges."     
C. Trent Barclay: "This is the first black president, one who was a cultural consumer during the rise of hip-hop. Can we put Eminem or Odd Future on the list? Of course not. But established, conscious acts that resonate with Gen Xers and older millennials feel essential. Given middle America's wariness around the artform, I'll vet each choice to make sure we're associating the boss with artists who are outspoken, but not too outspoken. Hey, and guys, I think it'd be funny if we at least snuck one Odd Future member on the list!" 
D. April Phillips: "Obviously, given the Spotify platform, this is a play to the younger block. At the same time, we're talking about a 54-year-old man who smoked pot in the '70s. For believability's sake, this can't appear as if a team of 20something interns crammed their favorite songs onto the list. We need Boomer staples; we need timeless, eternally cool classics; we need to make sure we're not marginalizing the tastes of the voters who — pardon my candor — actually matter: the ones with money to donate to Hillary."
Answers: D; D; C; D; D; A; D; D; D; A; A; C; C; D; D; A; B; A; A /// D; B; D; A; D; A; C; D; D; C; D; D; D; D; A; B; C; D; D; C

[Disclaimer: We have no idea who chose Obama's playlist — coulda been Barry! All of the above "interns" and their quotes are 100 percent fictional.]