Music

Little Talks - Of Monsters and Men is, lyrically, a conversation between two people.

One Bourbon, One Scotch, One Beer - George Thorogood is like a dude telling a story, with a bit of song in between the story.

Same with Alice's Restaurant Massacree by Arlo Guthrie, but a funnier and longer story.

I know a lot of love songs that sound like they are someone talking to a person, which is what I thought of seeing Jolene in your list. I don't think what you're after is a specific genre though, and given the examples I could probably just list every single song I have favorited on Spotify that isn't purely instrumental.

Leonard Cohen - Famous Blue Raincoat

The video starts off NSFW. Pillow Talking by Lil Dicky featuring Brain

It's a post-sex conversation between two people who presumably met on a hookup app.

Left Handed Kisses - Andrew Bird feat Fiona Apple

Tom Waits - Christmas Card from a Hooker in Minneapolis

Some classics I didn't see here yet:

Pink Floyd - Wish you were here (all the songs from that album, come to think of it, are in the second person and usually pretty specificially talking to Syd Barrett)

Bob Dylan - Like a rolling stone

Now for a completely different take on "feeling like a conversation", I have an instrumental recommendation: Bernstein and Brubeck - Dialogues for Jazz Combo and Orchestra

Edit: just noticed that a lot of songs by Steely Dan are also in the second person, usually directed and criminal or tragic figures. Kid Charlemagne is my favorite in that format.

Telemiscommunications - Imogen Heap + deadmau5

Hi Ren by Ren

I mean it might sound an obvious choice but 'She Loves You' by The Beatles is basically this.

Bohemian Like You - The Dandy Warhols https://youtu.be/ZJLDjYRfx3g

A dude trying to chat up someone he likes

Another Customer by Andy Ditzler

A guy talking to himself or to another person who is on the phone with customer service, and then while on hold starts to ponder about life.

Admit it by Say Anything The Noose by A Perfect Circle Never there, rock and roll lifestyle, or Walk on By by Cake (they do this a lot) Kiss me I'm shitfaced by Dropkick Murphys Save Tonight - eagle eye cherry The Most Beautiful Girl (in the room) - Flight of thr Conchords

This might be what you're looking for. Basically a monologue over a scratchy beat

Baz Luhrmann - Everybody's Free To Wear Sunscreen

"Somebody That I Used to Know" by Gotye

"O.G. Original Gamer"by MC Lars

"I'll Form the Head" by MC Frontalot

(Actually a lot of MC Frontalot consists of him arguing with other people.)

Clutch is a stoner rock band with some really unique lyrics - Neil Fallon has the manic poetry of someone who has seen The Truth and has lived to tell the tale. The first 3nsongs of their 2015 album Psychic Warfare are presented as the singer recounting a weird tale to the authorities after the fact.

The Affidavit is spoken word opener where a cop or someone asks the singer to just write down everything that happened.

X-ray visions launches into the tale pychi warfare, conspiracies and the vengeful spirits of Ronald and Nancy Reagan.

Firebirds continues the tale: the singer encounters a strange girl who demands classic automobiles and energy weapons or else.

For extra credit a subsequent album revisits the same speaker years later trying to explain it all to his young son - In Walks Barbarella

Probably most clutch songs have this storytelling style and I can't recommend them enough

Interesting idea :) Gonna have to think about this one.

Not sure this song qualifies, but it does feel like he's expressing his frustrations to someone.

Kane Strang - My Smile Is Extinct

Emo?

This one’s fairly new but I really like it.

https://song.link/i/1683111979

Coffee Conversations by FUTURISTIC & Oswin Benjamin

A lot of Bruce Springsteen’s songs are like that, but I’ll recommend one in particular that hits your mark:

Brilliant Disguise. https://open.spotify.com/track/0nqbZ17t9v52SCemAm1QP0

Here are some that came to mind for me, some might be closer to what you are expecting than others, but I feel like they fit the description decently.

Father John Misty - Mr.Tillman

• The entire song is from the point of view of a hotel front desk clerk asking a guest about his odd behavior during a previous stay.

James and the Shame - Believe Me

• Rhett McLaughlin of Good Mythical Morning fame's solo project where he details his struggle with his changing religious beliefs after a lifetime in the church and how he feels others see him now.

Bo Burnham - FaceTime with My Mom (Tonight)

• Part of Bo Burnham's comedic yet serious special, Inside, he filmed and produced all by himself during the Covid lockdowns.

Head East - Never Been Any Reason

• The singer asking trying to make up with his partner about being on the road for long durations and she feels like there is no reason to think about here when he is on tour.

Sheryl Crow - All I Wanna Do

A story telling describing drinking at a bar at noon during a workweek when the man sitting next to her starts a conversation.

A lot of rock operas do this, Ayreon is one of my favourite projects here.

To pick one, The Human Equation is about a character in a coma, and has external and internal characters. Day Four: Mystery is his friend and his partner discussing the mystery of the car accident that put him there: https://youtu.be/fzsKhT3wHgI

Ben Folds (with Regina Spektor) - You don't know me

This song fit the bill? Very fun and catchy! Pamplemousse - Bust Your Kneecaps

The first one that came to mind is a wife and mistress talking.

Does He Love You by Reba McIntyre - https://youtu.be/FUP9DnurODw

Tom Waits - Martha

Would Everybody's Free by Baz Luhrmann count for this? (You might know it as "Wear Sunscreen")

You should check out Casiotone for the Painfully Alone. A lot of his songs are like this, the rest tend to be short stories set to music. Excellent band ( although I think it's just one guy named Owen Asheworth). He calls the project Advanced Base now, also really good

Setting Sail, Coming Home by Darren Korb. For the game Bastion, by Supergiant Games (developers of Hades + a few other cool games).

Henry Rollins - Liar might hit on that.

Robbie Williams, Nicole Kidman - Somethin' Stupid

Haunt Me by Sansa

upbeat loss

Dear Coach’s Corner by Propaghandi is an open letter to Rob McLean about Don Cherry and other issues in hockey.

Said the King to the River - La Dispute

Song for a chicken named Jenny - Pat the Bunny

‘The Business Man and ‘Atlanta’s Own’- The Taxpayers - The album ‘God, forgive these bastards’ may have a few like what you’re looking for.

Carolina Drama - The Raconteurs

I do this all the time by Self Esteem is one that comes to mind

Dear McCracken is great!
Orange Juice by Noah Kahan

BB King - Lucille

maybe ME! (Brenden Urie and Taylor Swift, probably only kinda counts) and Just Give Me A Reason (P!nk and Nate Ruess)? I think Like I'm Gonna Lose You (Meghan Trainor, John Legend) might also work?

XTC - Dear God