Over more than 20 years as both a solo artist and leader of Americana stalwarts Old 97’s, Rhett Miller has made a career of telling stories about love, heartbreak and bad decisions.

While those may not be the standard ingredients of holiday stories, all of them are likely to make an appearance as he and friends like comedian Dave Hill and author Ben Greenman come together for Miller’s fourth annual holiday extravaganza at City Winery on Nov. 28.

amNewYork spoke with Miller.

Where did the idea for a show like this come from?

I’ve been a guest before on Wesley Stace’s show, the Cabinet of Wonders, and really liked the format. I’ve also been on a number of charity events, where it would be mostly comedians and a few musicians. That’s where I got the idea to do my own show, which I did in LA. It was called “Wheels Off,” and it was really kind of crazy. ... My go-to guest, my ringer, has become Dave Hill, who is so funny and is primarily known as a comedian, but is also the best guitar player I know.

Is it true you have an Old 97’s album that is nearly done?

It’ll come out in February. The last 97’s record was “Most Messed Up,” which people liked a lot. It was almost a concept record in that it was a no-holds-barred peek behind the curtain of life in rock ’n’ roll and all the attendant excesses ... This record has a lot more to do with God, and the idea of God as a vengeful punishing force. In a sense, it’s a logical continuation, but not in the way you might expect. It’s like the party ends and the next morning everyone is paying for it.

People see your songs as very autobiographical. Do you think they read too much into them?

Yes and no. I try really hard to be honest with the feelings and sentiments in my songs. The facts aren’t always true. I make a really strong point to divorce myself from the narrator so I don’t have to answer for whatever messed-up stuff the guy does or says. But I do try hard to be honest in terms of finding something at the core of a song that is a real human emotion and exploring it. If someone listens to a song I’ve written and feels like they know me, that’s a reasonable thing to think. If they think the guy in the song is me or everything he does is something I’ve done, that can’t be true. I’d be dead if I did all that stuff.

Do you have a favorite holiday song?

When I get together with musicians and comedians, we always end up talking about our least favorite song. I grew up in choirs. I’m not an overtly religious person now, but I still go back to something like “Silent Night.” If I take my kids to a candlelight service on Christmas Eve and we’re lighting the candles and singing “Silent Night,” I’m remembering Christmas Eve with my grandma, who passed on, and my family and being a kid myself. I always get emotional and choked up.

Since you brought it up, I have to ask about your least favorite song.

“Last Christmas” by Wham! is pretty insipid. There are worse songs. It’s catchy and hooky and it has a good melody. There are songs that are truly horrible, horrible songs. “Grandma Got Run Over by a Reindeer.” That just doesn’t make any sense. “I Saw Mommy Kissing Santa Claus” always gets a little awkward for me too.