1. “Step Into My Office, Baby” – Belle & Sebastian
Story! One balmy December morning (fall doesn’t start until December in Texas), after I took my only final exam of that semester, this song came on shuffle on my iPod. As I walked up the hill to my bus stop, the sun was shining through the quickly defoliating trees and the air felt like someone had left the fridge open. Of course, a hoodie was involved. This has remained a cherished seasonal memory in my mind, standing out as a time when everything felt a-OK. “Step Into My Office, Baby” is also a song about having inappropriate sexual relationships in the workplace. Feel free to enjoy it on either level.
2. “Waiting For Superman” – Iron & Wine
Grey skies and introspection will sound best with this. For flavor, add a dash of beard. It’s No Shave November, after all. As an Austinite, I rest assured that Dripping Springs resident Samuel Beam is singing this Flaming Lips cover directly to me.
3. “One Of These Things First” – Nick Drake
There’s going to be a lot of oldies on this playlist, by the way. Bassnectar doesn’t really go with apple cider. Much like Iron & Wine, you could put any Nick Drake song on this list. The contemplation! The quiet, folky guitar! The tragic shoegazing! It’s tailor-made for staring out the window and priming yourself for wintertime depression.
4. “Make Your Own Kind of Music” – Mama Cass
For those of us who are independent career women trying to make it in New York City in the late 1960s, this song strikes a particularly wonderful nerve. Maybe it’s because I’m really close to my mom and we listened to the oldies station incessantly when I was growing up, but this is a darn fine tune for those bright, post-Daylight Savings Time mornings. Let’s shatter the glass ceiling and wear pillbox hats, girls. You know Peggy Olson would do it. If you’re already a “Lost” fan, then you’re ahead of the game.
5. “Old Pine” – Ben Howard
Like Nick Drake and Iron & Wine, another folky jam with guitar-strumming action — quelle surprise. For this bro favorite song from ACL standout and English person Ben Howard, imagine barefootedness and tent-pitching, with seasonal beer flowing like … beer, I guess. Build a campfire next to your laptop. You deserve it.
6. “Pinesong” – A Fine Frenzy
Another fall favorite: spookiness. Like dark magic practitioner/Fleetwood Mac vocalist Stevie Nicks before her, Alison Sudol captures that ethereal, misty aesthetic like a pro. Halloween is over, but chances are you have some more candy laying around your office drawers. And your pockets. And your bed. Give your diabetic coma the proper soundtrack as winter fast approaches.
7. “Annie You Save Me” – Grafitti6
Nah. This doesn’t have anything to do with autumn. It’s November right now, and I just really love this song. Ergo, it is now a fall song. I just wanted to share it, that’s all. Carry on.
8. “Human Nature” – Michael Jackson
Michael is always in season, and the chillest song in his discography is the perfect stopgap until it’s socially acceptable to play the Jackson 5 Christmas album every day. Cue “Human Nature” up on the iPod, make some babies, and it’ll be like your kids get two Christmases a month apart.
9. “O-o-h Child” – The Five Stairsteps
Speaking of putting a little soul into your brisk autumn days, nothing is a better complement to brisk walks than Tupac’s favorite sample material. Since at least half of the songs on this list will make you incurably depressed, even it out with this one. Brass on brass on brass.
10. “Re: Stacks” – Bon Iver
Fall is the only reason that God created Bon Iver. “Re: Stacks” is unequivocally my favorite Justin Vernon ditty, because it makes me think about plaid and drizzle. That could be said of any Bon Iver joint (except any of his collaborations with Kanye), but this one in particular will gut me every time. It helps that it’s impossible to tell what he’s saying. Did I mention this was a Bon Iver song? Bon Iver.
11. “Come Thou Fount of Every Blessing” – Sufjan Stevens
Technically a normal hymn and not a noel-specific song, but guys, it’s basically Christmas already. If Starbucks already has the red cups out, I already have the Sufjan yuletide collection in my Spotify play queue. Settle in and feel the joy.