The holiday season is Ana Gasteyer’s time to shine. The Saturday Night Live alumna, who is also a classically trained vocalist with Broadway credits including Elphaba in Wicked and Queen Aggravain in last year’s revival of Once Upon a Mattress, says that she loves how this time of year “lends itself in a very comfortable way to throwback nostalgia, without being hokey.” It’s why holiday tunes are such a natural fit for her vocal style. “When I’m performing, I’m drawn to the American songbook and standards from the 1950s and early ‘60s, because they have a lot of comedy built in,” Ana tells Westport Lifestyle. “There’s the interchange with the band, and I have a big voice that does well with horns. Basically, I would have been really happy being an entertainer in 1958,” she says with a laugh. With all that in mind, in 2019, she recorded a holiday album called Sugar & Booze, which features a mix of seasonal staples like “Have Yourself a Merry Little Christmas” and “Sleigh Ride” and original songs like “Nothing Rhymes With Christmas” and “Secret Santa,” a duet with fellow SNL alum Maya Rudolph. (“We wanted the music to be original, but feel seamless with the era,” she explains. Case in point: the album and title track are named for what she deems the two best parts of the holiday season. Find a crooner who wouldn’t agree.) The record was so fun to make that she started taking it out on the road during each subsequent holiday season. “As an entertainer, I love the sense of sort of hosting a big Christmas party,” she says.
Happily for Westport, that Christmas party will hit the Westport Country Playhouse stage on Monday, December 22 at 7 p.m. “It’s a very happy, festive, easy-to-listen-to record, and that has evolved into a celebration [on stage],” explains Ana. “I love doing this show, and I’m always so moved that people want to come and celebrate with me. We give away prizes, come up with games for the audience, and I always encourage festive outfits. It’s my happiest place: throwing an entertainment party.”
And while this may be Ana’s first time performing at the Playhouse, it’s not her first holidays-and-Westport connection: in 2017, she played Mrs. Schwartz in A Christmas Story Live! and Westport’s own Justin Paul, along with his songwriting and composing partner Benj Pasek, added a song to their musical written just for Ana, “In the Market for a Miracle,” which she recorded for Sugar & Booze with Pasek & Paul’s blessing. “It was a very special career moment [to have them write me a song],” she says. “I felt like Debbie Reynolds or something!”
If you’re starting to get the sense that this time of year is meaningful to Ana, you’re right: it genuinely is. “My mom has always been very traditional about Christmas, and so I take [this time of year] really seriously,” she says. “I just lean into it.” And though Ana has spent many a Christmas working, she knows how to throw a good party. Her top entertaining tip: keep it simple. A holiday ham surrounded by chutneys, jams, mustards, and “really good bread,” plus beer, wine, soda, and a batch-made signature cocktail come together for a party that’s impressive and festive without being labor-intensive. (All that time playing Martha Stewart on SNL must have paid off.) “[Christmastime] has become this accidental recurring theme in my life,” she says. “My first breakout at SNL was Martha Stewart Christmas.” Add the legendary holiday-themed NPR “Delicious Dish” sketch “Schweddy Balls” and her SNL work is in the all-time Christmas episode pantheon.
Suffice it to say, Ana knows holiday entertainment. So don’t miss stopping by her get-together at the Playhouse. “What’s so special about the holidays is a sense of tradition and remembering something,” says Ana. “The holidays are a time that people let go, connect with each other, and forget about their cares to come together as a community.”
Ana Gasteyer - Sugar & Booze Holiday Spectacular, December 22 at 7 p.m. Tickets, from $95, at westportplayhouse.org