Think of caroling, and jolly, smiling singers decked in red and green attire belting “Jingle Bells” probably come to mind. 

But for Chicago’s professional caroling groups, holiday cheer is not just a hobby — it’s a lifestyle. Patrons often book Chicago caroling groups months in advance to come costumed and ready to perform any musical style. While some formal venues like corporate parties call for hymnal arrangements, more casual performances celebrate Christmas pop classics.

Bill Kavanagh, director and owner of Holiday Harmony Strolling Carolers, said his carolers have a vast musical repertoire.

“We can sing anything at the drop of a hat,” Kavanagh said. “Sometimes, there are people that bring up music to us and say, ‘Here, can you sing this?’ and they bring you a whole new arrangement.” 

Emphasizing the importance of participation, he said caroling should be interactive — a back-and-forth process between singers and audience members. 

Kavanagh said sometimes the music can elicit profound emotional reactions.

“A table asked for this innocuous Christmas song, ‘Jolly Old Saint Nicholas,’” Kavanagh said. “This older gentleman burst into tears, and it turned out that it was his late wife’s favorite Christmas song. Music brings up all this emotion, which is extremely touching.” 

Jeffrey Deutsch, former music director for the Classic Ring Carolers, said the job of musicians themselves is more than meets the eye.

“Singing for three hours starting at 7 a.m. is tough,” Deutsch said. “We also get together and rehearse only a time or two, and then we’d be sent out in quartets.” 

Traditional caroling consists of a four-part harmony with soprano, alto, tenor and bass voices, which blend to create a uniform tone. But carolers’ voices are not the only thing in sync.

Jaclyn Brown, executive director of The American Caroling Company, upholds strict costuming standards for her performances, depending on patrons’ demands.

“The traditional Victorian look is our most popular option,” Brown said. “But we do holiday sweaters, we can do all black, whatever clients want.” 

The joy of caroling lasts far beyond the holiday season for musicians, who have a deep passion for what they do. 

While business picks up in the fall months for a fully-booked December, carolers don’t stop after the holidays. Rose Colella, jazz vocalist and owner of the Lola Bard Carolers, operates her business year-round.

“People reach out as early as January for the upcoming season, especially those who are repeat clients,” Colella said. 

Colella, who expanded her Chicago-based company to Los Angeles, said responsibilities include responding to client inquiries, signing contracts, organizing payment for carolers, ordering costumes and sorting out logistics.

As a whole, Colella said the process is intensive but worthwhile. 

“How many other jobs are there where every single person who passes you — their face lights up, they want to take a picture of you, the kids are elated and start clapping,” Colella said. “It’s just constant joy, and it’s really rare to have a job that brings people that much joy.”

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Twitter: @charlottehrlich

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