It’s not so much a mix-tape because TheGloss staff is not 15, it’s not 2001, and we’re not trying to ask you to homecoming. We’re just trying to share some super cool music that we listen to while staring out windows drinking scotch pensively. Arm yourself with some cream cheese and book yourself into the Essex House for a week before breaking this out. Alternatively, host parties wherein you play only the following. Theme that party. For the sake of appropriateness, make the theme “a terrible party.”

[youtube=http://www.youtube.com/watch?v=x6RwSsHSIfs?version=3]

Billie Holiday, an actual depressed person.

[youtube=http://www.youtube.com/watch?v=-x622P_G1_c?version=3]

The Magnetic Fields singing about Billie Holiday. Presumably, they are not a bunch of sunshine kiddies themselves.

[youtube=http://www.youtube.com/watch?v=V3okiWGqKiA?version=3]

Not as much about literal Maps as you might expect.

[youtube=http://www.youtube.com/watch?v=osoeMtSbxtU?version=3]

I know you think you’re the Queen of the Underground. (Ashley and I have concurred that Wild Horses is MUCH more depressing, we just really like this song).

[youtube=http://www.youtube.com/watch?v=8kwJaFnmHo4?version=3]

Jamie correctly points out that this song is FUCKING DEVASTATING.

[youtube=http://www.youtube.com/watch?v=BrZTNhW44-o?version=3]

Maybe nothing is sadder than falling off a mobile home.

[youtube=http://www.youtube.com/watch?v=DVNlQ3ajqFk?version=3]

This is one of my favorite sad songs and I am pretty fucking psyched that there is a comment on the youtube video that reads “Why does this song remind me of the Duchess of Marlboro (Consuelo Vanderbilt)?” Because you and I are the same person, absolutely crazy listener. Also, this song clearly has nothing to do with Consuelo Vanderbilt.

[youtube=http://www.youtube.com/watch?v=3Dsz4dB6DuM?version=3]

Universal agreement: this song will make you kill yourself.

[youtube=http://www.youtube.com/watch?v=exJ3AG0JIeo?version=3]

“Anything by Sharon Van Etten” is also a fair answer.