Dean is still riding the high off his first single, "Going Well," which is doing shockingly well. It debuted at number one on the Billboard Top 100 chart, marking his second song to top that chart and the first to do so for multiple weeks — it dipped to number two its second week, but bounced up for the third, and now is on track to hit its second week in a row at number three. As if that's not impressive enough, it's also topping the radio on multiple formats, and there's a Tik Tok trend going on with the song, too.

This is the best performance of any song he's ever released. It's not even a debatable fact. Sure, he's no Ariana Grande, but this is great. In fact, the song is doing so well, his publicist has even started adding new interviews and performances to his schedule to keep the promo up, because it seems to be paying off.

They're nearing the end of week five of this song, and he should be releasing the second single soon. Unfortunately, to do that, they would typically pull the first song from the radio to promote the new one, and no one wants to kill the hype around "Going Well," so they're holding off on the next song for another couple weeks. It's much easier to focus on one single at a time. They have to get it out soon, though, because Christmas songs are about to start dominating the charts again, and he can't compete with Mariah Carey.

Because the success this era has generated already, Dean's publicist has already decided to hook him up with BBC's Live Lounge for the first time in a few years, hoping to make the most of his new exposure. For anyone who doesn't obsess over popular artists and their performances, BBC's Live Lounge is a pre-recorded performance with a set list of four or so songs from the artist's catalogue, and one cover of another artist's songs.

Last time he was there, he covered Lynyrd Skynyrd's "Simple Man," which was the last time he managed to get away with it before his fans decided they were sick of hearing that song over and over. He's going to need to pick something different for this year's performance. The question is, what?

Naturally, he takes to his phone to ask around.

Dean: Hey since you were really good at suggesting TV shows to watch can I ask another favor

And now he waits.

And waits.

And waits.

Castiel must not be anywhere near his phone right now. Unfortunately, Dean doesn't have anything to do for the rest of the day, so getting a line on Cas was his only chance at entertainment. Now he has to find something else to do.

So he starts watching Lucifer. Castiel's IMDb listed him as a character in a couple of episodes, both early in the series. That's about all the motivation he needs to convince himself to watch it.

~~

It isn't until that night that Dean finally gets a text back.

Castiel: Sorry, I was on a "date" with Jo. Are you still looking for a favor?

Finally! God, he was starting to think he was going to finish the show, or at least the first season, before Castiel got back to him.

Dean: Yes I am

Dean: But you can't tell anyone

Castiel: I can't tell anyone we're talking at all, to be fair.

Castiel: Wait, do you mean I can't tell anyone at all? As in it's a secret from literally everyone, including Jo?

Dean: Oh no you can tell her but my publicist would murder me if she found out I was talking about this

Castiel: ... okay?

Dean: I've been booked for the Live Lounge in a couple weeks and I need something to sing

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: :)))