Music fans first encountered Darren Criss when he starred in Glee, putting his own spin on hits like Katy Perry’s “Teenage Dream.” Since then, he’s had an Emmy-winning turn on prestige television (The Assassination of Gianni Versace: American Crime Story), starred on Broadway, and debuted a pop EP, 2021’s Masquerade. He follows those accomplishments with a fresh, singular take on the holiday album, pulling together classic tunes alongside left-of-center choices like John Mayer’s “St. Patrick’s Day” and Regina Spektor’s “New Year.” Unexpected arrangements and acrobatic vocals abound, making A Very Darren Crissmas one of an elite few albums that add value to an increasingly crowded field. “I tried to inject as much of myself and nostalgia from my own experience of the holidays and offer that as a gift for people as they create their own traditions and experiences,” Criss tells Apple Music. “So, the album is as convenient of a pun as it is a very true statement—it is undeniably, uniquely, and inexplicably a ‘me’ Christmas.” Below, Criss walks Apple Music through a few favorites, new and old. “Happy Holidays/The Holiday Season” “It definitely sets the scene. I was surprised when I found out that there weren’t as many covers of ‘Happy Holidays/The Holiday Season’ as I thought there were. Andy Williams is one of my personal favorite voices during the Christmas holidays. He had his Christmas special on TV for years in the ’60s, and I loved those. I really try not to cover songs that have had hundreds of other famous recordings, so I was really excited when I found out there weren’t that many. So, this one is really a bit more on the nose, to honor him.” “(Everybody’s Waitin’ For) The Man With the Bag” (feat. Adam Lambert) “I really wanted to make this a fun, ‘two guys with their drinks in hand and bow ties undone’ kind of a feel. I think you have to have a good jazz ear to make the song work, because it’s full of tight, chromatic runs. I wanted to have somebody whose pedigree could really elevate that because, again, the harmonies are tight and it’s not an easy tune to do. This is a very ‘me’ Christmas album, so every decision on this wasn’t just some random call. This is me asking friends to do stuff, and bless his heart, he was all about it. Adam is primarily now known for Queen and pop singing but comes from more of a jazz background. So, he was really thrilled to have an excuse to put that hat on again and sing this with me.” “St. Patrick’s Day” “One of my main goals for this album is to take songs that are evocative of the holidays that aren’t necessarily on the Christmas playlist and give them a fair shot by contextualizing them in a Christmas album for people to say, ‘OK. This is, in fact, a holiday song.’ ‘St. Patrick’s Day’ has always been one of my favorite John Mayer songs. I think he’s one of the great songwriters of our time. I love the bait-and-switch of the title, because you look at it and you’re like, ‘This is a Christmas album. What the hell is ‘St. Patrick’s Day’ doing on here?’ And then, as you listen to the song, there’s this really satisfying payoff about falling in love during the wintertime and wanting it to last through the winter to get to the spring, which is right around St. Patrick’s Day. It’s the finish line.” “Somewhere in My Memory” (feat. Evan Rachel Wood) “Evan and I have been great pals for a long time. We have shared a lot of fun parallel paths with our love of theater, musical theater, and doing rock ’n’ roll music, but also being actors. We relate to the same culture that reared us. So, Home Alone, obviously, is a big movie for both of us, so that song holds a certain amount of weight. There are some really interesting covers of the song online, some that I really liked, and so I figured I would make it more of a duet but try and make it as true to form as I could. Evan is a very versatile singer, where she can do legit Broadway singing but she can also do punk rock singing or pop singing. I told her to go full ‘concert hall, classical, church soprano belt shit’ because I was like, ‘How often are you being asked to do this?’ ‘Never.’ ‘OK. Blow the roof off. Go nuts. You don’t have to be sweet on this one. This needs to be just beautiful.’” “Drunk on Christmas” (feat. Lainey Wilson) “When I met Lainey, I realized very quickly that this song was actually an alternate-universe song where ’70s Dolly [Parton] did a duet with ’60s Dean [Martin], a rascally duet about being drunk on Christmas. I think it would have been a total coup. So, this was my attempt at rewriting history and trying to do a version of that, the jazz-pop-rock guy and the country gal getting together and having a cup of something naughty.” “New Year” “I think ‘New Year’ is the crown jewel of the album. It’s the one that [producer] Ron Fair and I are the most proud of, for a variety of reasons. One, I think it is a song that most people will be hearing for the first time. Which, as a Regina Spektor fan, I’m really happy to be able to put a spotlight on her work. I sent it to Regina, and she was happy with it, so I was very happy to get the seal of approval from her. You think the song is going to be very sad, about saying goodbye and somebody being by themselves on New Year’s Eve. But it’s actually quite optimistic, because this person is thankful for what they’ve been given and they’re not thinking about the things that they don’t have. They’re glad to be part of this moment and glad that they get another one.”