Castiel: I'm sorry to break it to you, but I am not an expert on your discography.

Okay, apparently Castiel is one of those people that has no idea what the Live Lounge is. Dean probably should have anticipated that.

Dean: I was already given a list of my own songs to sing, but I get to pick one song that isn't mine and I don't know what to pick so help

Castiel: I don't listen to the modern pop radio enough to know what's popular.

Dean: Dude Taylor Swift sang a fucking Phil Collins song in 2019 I promise no one cares if it's popular

Castiel: Oh.

Dean waits impatiently as the three little bubbles appear and disappear repeatedly. He's either typing and then deleting something over and over, or he's writing something very long and needs to keep pausing to think. Maybe he's switching between messages and Spotify to pick his favorite songs or something. Dean has no idea. So, while he waits, he unpauses Lucifer.

And then Castiel finally responds.

Because why would Dean get to watch his show?

Castiel: I don't really know how to answer this because I don't know much about your taste in music other than that you like Led Zeppelin and you make pop music.

That definitely does not take as long as he took to type. Does he feel weird? Is this a weird question? Now Dean feels kinda bad. He would have asked someone else if he knew Castiel wouldn't want to answer, but it's a bit late for that.

Dean: It can be literally any song as long as I haven't sung it before. You can even pick a song I don't know and I'll look it up. Just hmu with your favorite song

There's a long pause before Castiel starts typing.

Castiel: Do you like James Taylor?

Wow. He's really looking for a throwback. James Taylor's isn't quite the genre he's into, but it's around the right time frame, so he'll give the guy that.

Dean: I like some of his songs. Which one are you thinking of?

Castiel: Fire and Rain?

Huh.

He wasn't sure what he had expected from asking Castiel for help, but Fire and Rain was certainly not it. Fortunately, Dean already knows some of the song — everyone knows the chorus, after all, and he has a general idea of the melody to the verses — so he can swing this one.

Dean: See that's why I asked you

Dean: I knew you were gonna have a unique answer and not "go sing Beyonce's new song" or something

Castiel: I don't even know Beyonce's new song.

Dean: She probably doesn't even have one idk that's not the point

Castiel: There was a point?

Ouch.

Dean: Just that you have an interesting choice in everything and I appreciate it

Castiel: Thank you?

Dean: Why Fire and Rain tho that's kinda out there

Castiel: I don't know. I've always liked the song. Maybe you can bring it back to a younger audience.

Dean can't help but smile to himself. That's exactly why he chose to sing "Simple Man" as his redeeming performance on the Ellen Show the first time he was there. He had assumed he wouldn't make it very far if he didn't try to draw attention to himself by covering a popular song, and Sam had suggested over and over that he pick something by Taylor Swift or Ariana Grande because their fan bases are both huge and scary, but he wanted to remind people that Lynyrd Skynyrd existed. He said it right there on the show — "Boomer music deserves to live on."

Dean: I will 100% try it but I guarantee there will be hundreds of people who say mine is better than James Taylor's not because I'll be very good but because they love everything I do

Castiel: That's okay. It's a good song, regardless of who sings it (unless, of course, that someone is me in the shower, in which case it is not a good song).

Dean bursts out laughing. He didn't take the guy for a singing-in-the-shower type, and he definitely didn't take him as the admitting-to-singing-in-the-shower type. You learn something new every day.

Dean: Then it's settled. Fire and Rain, welcome to the 21st century!

Dean: Oh hey while you're here I wanna let you know that I started watching Lucifer bc I know you're in a few episodes and I'm a supportive friend and I'm actually obsessed with this show

Castiel: You obsess over shows very easily, don't you?

Dean: ... well now that you say that

Dean: But for real tho I relate to Lucifer on a spiritual level in everything he does

Castiel: It's been a few years since I watched the show so I don't need remember it very well, but wasn't one of the first very first episodes him trying to kill a guy?

Dean: Uhhh yeah but it was a criminal so it was okay

Castiel: ...

Dean: It's the law of the land, baby!

Castiel: Actually, the laws of this land forbid murder under any circumstances excluding self defense.

Dean: Don't bring your facts into this argument

Castiel: ...

Dean: :)))

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