When Emmy Award-winning actor and singer Darren Criss first started planning his holiday album “A Very Darren Crissmas,” he knew he wanted it to be a little idiosyncratic. “My general ethos is to be as left-of-center as possible while still making it feel accessible,” he says. “I didn’t want to just do a run-of-the-mill holiday album that anybody could do.”
The resulting album, released in 2021, boasted its share of seasonal classics like “Happy Holidays” and “Have Yourself a Merry Little Christmas,” but it also contained unorthodox choices like covers of John Mayer’s dreamy new-relationship song “St. Patrick’s Day,” Regina Spektor’s moody “New Year,” and a jaunty holiday version of Joni Mitchell’s melancholy classic “River.” There’s the oddball 1950s novelty song “I Want a Hippopotamus for Christmas” and the jazzy duet “(Everybody’s Waitin’ For) the Man with the Bag” performed with Adam Lambert. Criss even wrote a few original tunes, the fizzy “Drunk on Christmas” and the anthemic, brassy bop of “Christmas Dance,” both homages to a grab bag of festive classics.
Last year, Criss brought his “A Very Darren Crissmas” tour, inspired by the album, to the Wilbur Theatre. He’ll be returning to Boston with that holiday show Dec. 7 at the Emerson Colonial Theatre.
“These are all artists and records that really stuck with me as I grew up,” says Criss about the songs he chose to cover. Listening to those albums over the years, he took an inventory of how he might make his own record that was specific and personal to him.
“Christmas albums are one of the few remaining places where mashing up different styles and having music from different time periods is actually encouraged,” Criss says. “I’m a genre-phile, so it’s an amazing playground for a guy like me that thrives on eclecticism and strange and weird choices. It suits my musical proclivities very well.”
“I also wanted to make a collection of songs you already knew, but do them in a way you never expected,” adds the actor, who won an Emmy in 2018 for playing spree killer Andrew Cunanan in “The Assassination of Gianni Versace: American Crime Story” and who had a trailblazing role as a gay teenager on “Glee.” His Broadway credits include “Hedwig and the Angry Inch” and “How to Succeed in Business Without Really Trying.”
In creating his rendition of Mitchell’s mournful “River,” he took a poignant tune, about grappling with heartbreak at the holidays, and turned it on its head with more buoyant arrangements and some Motown-style grooves and harmonies to give it a different vibe. “If anybody gets their Christmas feathers ruffled by something on this record, it’d probably be that one,” Criss says. “I kept saying to myself, I don’t want to sully this song. But I’m not Joni Mitchell. So why have that work against me? I have to find a way to make things that work for my sensibility.”
Criss says he’s been a big fan of Mayer’s “St. Patrick’s Day” since it came out in 2001. “That song subverts your expectations,” he says. “It’s about falling in love in the wintertime as the holidays begin and it gets colder and more romantic, and you want to hold onto that winter love until spring starts to roll around.”
With Regina Spektor’s “New Year,” a high point on the album for Criss, he was aiming for another unusual choice, not “Auld Lang Syne” or “What Are You Doing New Year’s Eve?” The song is bittersweet, acknowledging what’s been lost but also projecting a message of gratitude and a sense of hope for the year to come.
As for “Drunk on Christmas,” a duet with country star Lainey Wilson, Criss dreamt it up while thinking of “alternate universe” — one part Nashville, one part Vegas — in which Dolly Parton sings a cheeky duet with Dean Martin about getting tipsy on Christmas. “It would’ve been an interesting coup to have these two beloved rascals, who have these very playful, cheeky natures, sing a country-pop crossover duet like this. In another universe, I would’ve loved to have pitched it to them.”
While he’ll be performing many of the songs from the album in concert, Criss promises that surprises will be in store. “I try to change every show I do,” he says. “I always have a section where I figure out a new song to play on that day. Now I think a lot of people have come to expect that — as much of a pain in the [butt] as it’s become for me to figure out a new song every single show. But in the age of YouTube, I want to make sure that I have a different fingerprint wherever I go.”
As an actor, Criss acknowledges that his banter game is big. So cabaret-style, in-between-song chatter and lively audience interaction is prevalent. “It’s like my little TED Talk,” Criss says.
Was the “Crissmas” pun of the title too irresistible not to deploy? “It’s unavoidable and painfully convenient. But I wouldn’t want to incur the wrath of people if I didn’t call it that. So I figured I might as well get ahead of it. But it’s a very apt title, because it’s indisputably me.”
Creating the album and touring the show altered his frame of mind, he says, “because I was constantly calling upon fond memories and really cherished moments in my life,” from belting out songs together with his family, watching his mom lip-synch to their favorite tunes, and making Christmas music mixes.
“I know the holidays can also be a source of great frustration for people. But all in all, it’s a pretty extraordinary construct that despite how terrible we sometimes treat each other and how many awful things happen in the world, that collectively as a human race, we have this one time of year that everybody is just trying to be a little better to each other,” he says. “As a painfully idealistic, happy-go-lucky kind of guy, that just makes my heart sing.”
A VERY DARREN CRISSMAS
At the Emerson Colonial Theatre. Dec. 7 at 7:30 pm. Tickets from $45. www.emersoncolonialtheatre.com, 888-616-0272
Christopher Wallenberg can be reached at firstname.lastname@example.org.