The 20 Best Conversation Songs of 2020

FRED DUST
8 min readJan 8, 2021

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Ps the title takes you to the Spotify playlist

A super amazing entirely gorgeous and fun New Year’s Eve playlist of the 20 best conversation songs I listened to in 2020

You’re gonna love them… and want to dance… and make dinner to it. I promise.

It’s New Year’s Eve and it’s the end of 2020. A year where amazing things happened that we never believed could happen. And while it’s been so hard for so many it’s important to enter the new year with hope and joy AND get some tips on how to practice making conversation

In no particular order.

Yes Its My First Solo Album

No 1. I Wonder by Shawn Mendes

Because it’s Shawn and that dance on the island that looks like Northhaven Maine running around with lost children who are now all genders and races. It’s an exploration of gender roles, an apology to his friends, and he’s in conversation with what… a children’s choir.

Pulling a Taylor, Shawn?

№2. Good Morning by Alex Aiono

Because the song is about just waking up and trying to find a way to make it a good day, whatever it takes. We need that conversation with ourselves every morning just to get through life, doesn’t matter when. The song deals with hardship and loss but still gets us up. Raised as a Mormon he’s in conversation with a… gospel choir of all faiths.

No 3. Tinsel and Lights by Tracy Thorn.

Because it’s a melancholic love song to… New York. I personally relate to her NYC martini experience but when I listen to this song I have a deep and undying love for the city I call home. New York, I still love you. And she’s in conversation with… Ben Watt? But I could be wrong.

Tracy and Ben in New York?

No 4. I Will Always Love you by Dolly Parton

Because it’s one of the greatest songs about forgiveness and love ever written paired with a very strong autobiographical bent as all great Dolly Parton songs are. In this heart-wrenching and mesmerizing song, Dolly is in conversation with… Porter Wagner who she was leaving.

No 5. Rainbow by Kacey Musgraves

Because Kacey is definitely speaking to all of us when she says “It’s hard to breathe when all you know is the struggle of staying above the risen water” but in the end, this country singer’s message is that there will be the rainbow we deserve. Singing this song with Kacey is like going on a 3-minute pilgrimage. In this song, Kacey is in conversation with…Me.

No 6. All I want for Christmas is You by Dolly Parton

Because Dolly gets raunchy with it, And she pretty much redeems “Baby it’s Cold Outside” which seems pretty innocent in comparison. And come on who can beat the conversational opener “You can go first…right after me.” In this song, Dolly’s in conversation with… Jimmy Fallon

No 7. Song for No One by Shawn Mendes

Because this is a love story about a conversation where the “poor” kid gets rejected. Maybe he shouldn’t have told the person he loved them but he probably should have. If you love someone, let them know. Oh and Mendes and tambourine…yes please! Ultimately this love song is in conversation with…no one or everyone. Take your pick.

Suki Loves You Shawn

No 8. Hard Candy Christmas by Tracy Thorn

Because this was the song that helped me discover Tracy’s Xmas album and I so love it. She’s singing about the fact that for so many of us, Christmas can be hard while reminding us that it’s time for a conversation about transformation. Lose weight, gain weight, get drunk, or don’t. Just talk about becoming. And in this song Tracy’s in conversation with… Dolly.

This is not Tracy Thorn

No 9. Betty by Taylor Swift

Because Taylor Swift is my spirit animal. I once ate next to her in New York and she was luminous. Folklore and Evermore were the soundtracks to my year. And Betty — the third part of a three-song trilogy of a Highschool affair — is just a stunner and ends with modulation in a song about heartbreak. It’s gorgeous and heart-wrenching all at once. In this song, she’s in conversation with… every shy and clueless teenage boy (all of us).

No 10. Betty by Josh Rabenbold

Because Taylor is being super open about covers of her work (And we know how she feels about music rights.) But she’s always been fairly generous about letting people cover her work including a complete cover of 1989. Here Josh’s cover gives us the boy singing his own song and he makes it so sweet and poignant. If you can’t feel his sorrow then you can’t feel. In this song, Josh is in conversation with… Betty or actually, Taylor.

No 11. The Last Great American Dynasty by Taylor Swift

Because every conversation deserves a short perfect 30-second story. This song sprawls decades but tells an amazing story in 3 minutes with a surprise twist at the end. Come on. You’ll never forget the song. And of course, in this song, she’s in conversation with… Rebekah? Westerly? I think the latter.

These songs are good to cook to

No 12. No Body No Crime by Taylor Swift

As a close friend would say “I can see your Taylor slip” meaning she gets three songs. Sorry, I told you she is a huge inspiration despite the fact that she’s stunning unbelievably wealthy, and a genius singer-songwriter. But this song takes the trilogy concept from Folklore and packs a perfect revenge story into 3 minutes. Each verse is a different woman with a different twist and it just ties you into a knot. And in this song, she’s in conversation with… HAIM and supposedly the trio agreed to sing it because of the Olive Garden reference.

No 13. Old Town Road by Lil Nas X and Billy Ray Cyrus

Because this is a conversation between two greats and it has all of the staples of a good country song. This song is compelling, short (not even three minutes), and once you hear it you’ll never get it out of your head. This kid genius did this remixing from an almost ubiquitous beat. Also gotta love Cyrus’ version of a horse. This song is in conversation with…Country Music.

This is Lil Nas X and This is Country

No 14. The Revolution Will Not be Televised by Gil Scott Herron

Because this is a conversation song about America and he makes a prediction about the U.S. that both is and isn’t right on the money. Sadly the televising of the revolution really is part of what is bringing conversation down. This song is so genius both because of the spoken poetry quality which converses with Rap music and so much else. In this version, Gil is in conversation with…2020.

No 15. Happy Ending by Alex Aiono

Because this 24-year-old kid is gorgeous and so talented. Watch out Taylor here he comes. But we need a song that’s in conversation with how lost we are and reminding us that we will have our Happy Ending. Though at 23 I’m pretty sure this is not the last Happy Ending Alex is seeing. Alex is in conversation with…2021 promise.

No 16. Piece of a Man by Gil Scott Heron

Because when I had my 3 am college radio show I pretty much played Gil nonstop and Pieces of a Man was the heartbreaker. It tells a story that’s so now that you’ll think he’s speaking from the grave. We lost him in 2011, but he was recording til the end. This song is a story song like none other and the plight it describes is so unbelievably relevant. Hang tight on this one, it’ll make you cry. In this song, Gil is in conversation with…anyone who’s lost their job this year.

No 17. I’m Going to Live the Life I Sing About in My Song by Mahalia Jackson

Because here’s the cure for heartbreak. The life she sang about was a pretty good life, lots of love, lots of perseverance, no bitterness, and not for gold or fame. The life Mahalia was singing about has resonance for all of us. Get to know gospel and get to Mahalia and your life will be better for it. In this song, Mahalia Jackson is in conversation with…i want to live the life i sing about in my song.

No 18. Song Along by the Cast of Eurovision

Because it’s Eurovision or at least a parody. But it’s amazing and it’s a melding of every Europop song you ever loved with an entirely global cast. And come on this is the kind of song harmonizing we need to have right now to bring global peace. The cast of this song is in conversation with…global unity.

No 19. Alcohol You in the Morning by Roxen

Because this is Romanian and awesome. I owe this one to Switched on Pop where Roxen promises “alcohol you when I’m drunk”. This song is sophisticated and utterly true. We’re all likely to drunk dial you at some point. We’ve all done it and we’ll do it again. In this song, Roxen is in conversation with…My Ex.

No 20. High Hopes by Panic at the Disco

Because I had to. We took you all over the map and felt like I owed you something that’s all hope. This song starts with a conversation with mama and listens to what she says; “make a legacy”. Mama is full of hope and good advice. Take this song with you into the next year. This song is in conversation with…your future. I promise.

Ok I’m Fangirling

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FRED DUST
FRED DUST

Written by FRED DUST

Founder of Dust&Co, senior design advisor for Rockefeller Foundation & former global managing partner of IDEO — fan of words and good conversation.

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