For Rainy Weekends and Halloween: An Autumn Broadway Playlist

Creating seasonal playlists is one of my favorite things, and I’m always really excited when I get to come up with a new one. But as it turns out, there really aren’t that many showtunes about fall! I don’t understand why people don’t like writing songs about rain, and fog, and being back to school… Someone should just write Sweaters and Homework: The Musical already! I know literally every high school and college student ever would love that.

For the time being, however, here are a few songs from musicals that are somehow related to the season anyway. Some of them are about fall, others just feel appropriate for quiet afternoons when it’s just cold enough for a sweater and you feel ready and willing to consume your body weight in tea and pumpkin spice lattes. I’ve also included some Halloween tunes to get you thinking about costumes and theme parties! I know Halloween’s a month away but it’s never too early to get excited, right? Plus, it makes getting through the dreary October so much easier!

  1. Autumn” from Titanic: The Musical
    I know, that’s a really sad song! Honestly, it kind of gives me chills in a way that’s pretty autumnal itself. But what I like to focus on is the first verse because the lyrics are so beautiful and hopeful. Despite the fact that the rest of the song, and frankly – the entire musical – are really, really sad, somehow the words “still, perhaps this autumn love won’t retreat in the autumn, all that we have won’t be past” are a good way to open a fall playlist.
  2. A Little Fall of Rain” from Les Misérables
    No, I’m not out to make everyone cry two songs into the playlist. I know that this song isn’t exactly relatable, thankfully, but there’s still something really fun about sob-singing “a little fall of rain can hardly hurt me now-w-w” on that one day when it starts raining while you’re on your way home and you somehow managed to forget your umbrella. You and I both know that’s happened at least once!
  3. Magic to Do” from Pippin
    You might be asking yourself how is that a fall song, but hear me out! A Pippin-themed Halloween party! Think about all the glitter and circus-themed decorations, and about the costumes that you and your friends could come up with. There’s practically no way to go wrong with the Pippin aesthetic around Halloween. And the lyrics to “Magic to Do” make an absolutely perfect party invite.
  4. Halloween” from Rent
    This really isn’t what I meant when I said “Halloween tunes” but this song from Rent is undeniably a must for every fall-related showtune mix. It’s heartbreaking and gloomy and it’s bound to make you sad every time you hear it but at the same time, Halloween’s a time for parties and celebrating, right? After all, it was Angel’s favorite holiday.
  5. Gold from Once
    Truth be told, Once is my personal favorite fall musical. This son’s very color scheme implies an autumnal mood in and of itself, and it’s such a fantastic song about love as well. This entire score absolutely perfect for a day where all you want is to curl up with a hot beverage of your choice, and listen to some acoustic music and beautiful harmonies, and maybe cry a little. Watching the movie that the musical is based on is also a great idea for a rainy afternoon, or even an evening shared with a couple of friends!
  6.  “Illness as a Metaphor” from Bloody Bloody Andrew Jackson
    Similarly to “A Little Fall of Rain”, this song is all you need for your overdramatic moments this fall. Yes, maybe you’re not president Andrew Jackson but I can assure you, from experience, that singing about your fever’s being your pain transformed into art, and a representation of your feelings, is actually hilarious. Trust me, it will make any seasonal cold or the flu a lot more bearable, and it could double as a love song as well! Also, emo Andrew Jackson is a good Halloween costume, don’t you think? It’s all metaphorical, you see.
  7.  “Say the Word” from The Unauthorized Biography of Samantha Brown
    This song always reminds me of falling in love in high school, and of cold October evenings spent outside talking to your crush. It might be the verse about windy nights that gives me that autumnal feeling, and every time I listen to this song, I think of that strange, gloomy melancholy that usually accompanies nighttime in the fall. High school romances and melancholy are essential for autumn, and in a way, they go hand in hand.
  8. Forever Autumn” from War of the Worlds
    Yet another song about autumn which toes the line between being creepy and being a love song. Everything from the arrangement to the narrative in this song create that perfect balance and make it absolutely ideal for rainy afternoons where feeling a little sad is just perfectly acceptable. But on another note, why are love songs about autumn always so sad?
  9. When You’re an Addams” from The Addams Family
  10.  To end this mix on a more positive note, I give you the quintessential Halloween song. I could’ve just given you the Addams Family tune (*snap – snap*) but I feel like this song can be all you need to get motivated and start thinking about your Halloween costume. Let the “how to be an Addams 101” guide inspire you, and go crazy with too-pale face makeup and slightly gothic clothes in black velvet, and there you’d have it: a Halloween costume which is both a classic, and musical theater related!

More Articles