Welcome to Playlists, a series where we turn over the reigns to artists to curate the next big playlist

A midlife crisis is characterized by an individual’s contemplation of growing older and inevitable mortality. Many grieve their loss of innocence through attempts to reclaim the past ⎯⎯ popular models include getting a mistress, buying a corvette or simply feeling stuck in first gear. But sometimes, looking back can be the fire you need to catapult you forward. We all must face impending doom sooner or later, and Kim Ware, of The Good Graces, muses on her place in the universe, from heartbreak to tragedy to renewal, on the group’s latest album Set Your Sights (out now). “You know I’m broken, too, ’cause the hardest thing to do is saying I don’t love you,” she weeps on “Broke on Two,” while “Out There” depicts the loneliness we feel from the greater cosmos. Later, she concedes on “The Hard Way”: “I don’t like cliches but sometimes I just am one.”

Ware explains of the record’s themes, “Sometimes, joking around, I call this my midlife crisis record. It’s about getting older, regret, feeling bad about things I’ve done in past relationships, and just trying to figure it all out. A lot of the sad relationship stuff — it’s my way of analyzing what went wrong. Making this record, I learned that, sometimes, coming to terms with something means accepting you might never come to terms with it.”

“People so rarely learn from their mistakes. Everyone talks about it, and it’s easy to throw that out there, but we so rarely focus on why we made a mistake in the first place. It’s important to not just treat the symptom but the underlying cause. I think that should be the bigger focus,” she adds.

Getting lost in the music and turning to a wide swath of stylistic pioneers, Ware has curated an accompanying Breaking Up is Hard to Do playlist, exclusively for B-Sides & Badlands. You’ll  find names like Death Cab for Cutie, Beck, The Psychedelic Furs and many others. Below, she also walks us step-by-step through the songs.

Hall & Oates – “She’s Gone”

I’m the biggest Hall & Oates fan on the planet. No really, I am. They are my favorite musical act ever, I’ve seen them live at least a dozen times and even got to go backstage once. I once met John Oates in a swimming pool in Myrtle Beach. So yeah, I have stories. Anyway, I couldn’t make a breakup playlist without this classic. It’s mainly the video that makes me love this song so much. But I remember singing it as a teen — the plaintiveness in the chorus is just perfect. I appreciate the directness of this song, too, the feeling that even if you move on to give your attention to something or someone else — “They can never be what she was to me.” And of course, awesome lines like “I need a drink and a quick decision” — and how many other songs do you know that reference “carbon and monoxide”??? So good!

S – “Losers”

Seriously, how heartbreaking a lead-off track is this? This entire album crushes me, and it was hard to pick just one song from it. But I think this captures that feeling of a moment so perfectly — going somewhere, seeing your ex and just feeling like shit (and props to S for also using the word “shit” in the song. I like songs that cuss when it’s the only word that will do.).

Death Cab for Cutie – “A Lack of Color”

Man, that Ben Gibbard can pen a sad song. I could have chosen many off this album too, and to be honest, it’s hard for me to even listen to this song. It just hits too close. So, I figure that means it’s doing exactly what it’s supposed to do.

Superchunk – “Like a Fool”

Superchunk is one of my favorite bands ever, and I was especially obsessed with their earlier stuff. The imagery in this song is really amazing. And it reminds me a lot of S’s “Losers,” in how directly it gets to that feeling. I remember reading how Laura would have the sound person take Mac’s vocals out of her monitor when they were touring for this album because it was too heartbreaking to hear lyrics about her. SO EMO.

Band of Horses – “Evening Kitchen”

DAMN THIS IS SO SAD. This is my favorite BoH song and really one of my favorite songs by anyone ever. It’s so perfectly beautiful and has just the right amount of space. Another song that references being afraid to go out because you’ll see someone you don’t want to see. So, I guess you just stay home and drink wine instead.

Beck – “Lost Cause”

‘Sea Change’ is one of those albums that affected me so much, so instantly, that I remember exactly where I was and what I was doing the first time I heard it. I was going through a breakup at the time, so I think I was particularly drawn to sad songs that seemed to be delivered from the perspective of the person doing the breaking up. Or at least songs that captured the resignation felt on both sides when you finally realize it’s just done. I think this song does that. This entire album will always be, in my mind, one of the saddest but most beautiful pieces of art ever made.

The Rosebuds – “Come Visit Me”

And speaking of sad, beautiful art. I could write pages on this album. Ivan and Kelly are old friends of mine. I knew them when they were starting the Rosebuds, and their band was SO FUN. They wrote songs that sounded like the Beatles and talked about holding hands at the carnival. So, it was pretty hard to hear their relationship had ended and pretty unbelievable to hear the art that came out of it, which is kinda the opposite of their earlier stuff. But the resulting album, ‘Loud Planes Fly Low,’ is their best, IMO, and another example of an entire album’s worth of songs that could fit perfectly on a breakup playlist. But I chose this one because it’s the only Kelly song on the album, or at least the only one she sings lead on, and wow, did she bring it for this one. I know too well (we probably all do) what it’s like to be in the beginning of a breakup, that time where you know it’s best not to see the other person, but at the same time you feel like they are the only other person on the planet who understands what you are going through. So, you see them anyway. Even though it makes it worse and fucks you up. Ugh.

Lisa Lisa & Cult Jam – “All Cried Out”

OK, I’m an 80s kid. (I almost included Richard Marx on this playlist. You’re welcome.) When this song first came out (the interwebs tell me it was in 1985), I remember thinking it really was the saddest thing I had ever heard, at least since Air Supply. And you’re also welcome for my not including “All Out of Love.” I was tempted but picked this instead. It’s funny now, but damn, IT’S JUST SO DRAMATIC. In reality, I didn’t have any relationship experience in 1985, and couldn’t tell you what it was like for your body to experience that much pleasure and your heart to know that much pain. But for four and a half minutes, you better believe I felt that shit.

The Psychedelic Furs – “Heartbreak Beat”

College. Thursday night. Fight with boyfriend/girlfriend. The only remedy? Dancing. That’s what this song is to me. This is the place you go to get through it. Or at least pretend you’re getting through it.

The Mountain Goats – “No Children”

Holy cow what an anthem this one is. I have an appreciation for anything John Darnielle has ever done, but I point to ‘Tallahassee’ as his best work. He’s a lyrical genius, and this song has so many great examples of that; every single verse is a testament to feeling like something is so completely over that the only respect you can pay to it is a song in which you actually hope that the other person can’t even say a single positive thing about it.

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