If you don’t think that Boston has a proud history of Christmas music, you weren’t there on that jolly night in 1857 at the Simpson Tavern in Medford, when a regular named James Lord Pierpont wrote a winter-themed drinking song and called it “The One Horse Open Sleigh,” though it soon became much better known as “Jingle Bells.” And this was just a few years after one of the most haunting religious carols, “It Came Upon a Midnight Clear,” was written by a Unitarian pastor in Wayland.

It’s a long jump from those holiday chestnuts to the songs on this year’s all-Boston Christmas playlist, which honors this city’s history of Christmas music, from seasonal depression to bawdy celebration. (You can find every song on Youtube, even if the records are long gone). We go in roughly chronological order and start way back in 1962:

Bobby Boris Pickett:  “Monsters Holiday”

You thought he was from Transylvania, but the “Monster Mash” guy really hailed from Somerville. He had his second and last hit with this ’62 number, where the monster gang plans a robbery of Santa Claus’ sleigh. All works out well of course, and Dracula still gets a new cape for Christmas.

Canned Heat & the Chipmunks: “The Chipmunk Song”

In the most bizarre Christmas collaboration ever, the ‘60s blues-rock group (cofounded by Arlington native Alan “Blind Owl” Wilson) crashes an Alvin & the Chipmunks recording session and enlists them for a “Christmas boogie.”  Proof that you could get away with anything after playing Woodstock.

The Snowballs:  “Come On to the Christmas Party”

Speaking of the Chipmunks, this festive blues number was secretly delivered to Boston radio station WBCN in the ‘80s. Even with the sped-up vocals, it was pretty easy to recognize the J. Geils Band as the true artists. Never appeared on vinyl or CD— but Youtube now hosts the original Chipmunky version and a digitally tweaked one where Peter Wolf sounds more like himself.

Billy Squier, “Christmas Is the Time to Say I Love You”

It wasn’t that hip for rock stars to do Christmas tunes in the 80s, but Wellesley native Billy Squier was having too good a time to care. This is one of the merriest and lustiest of all rock Christmas tunes, though its daredevil high notes make it tough to sing.

Kristin Hersh:  “Jesus Christ”

This joyous song, written by indie-rock hero Alex Chilton for his then-band Big Star, is perhaps the king of alternative rock Christmas carols. Even the Monkees wound up recording it, but there is no lovelier version than the one done in the ‘90s by the Throwing Muses frontwoman.

The Gravel Pit:  “Marshmallow World”

The local Q Division studio released its own compilation album “Viva Noel” in ’99; the surprise was that many of the artists gravitated toward the more downcast Christmas songs. This fondly remembered band was an exception, stomping their way through a tune originally done by a guy who knew how to celebrate: Dean Martin.

Juliana Hatfield, “Make It Home”

This was Hatfield’s big moment as a singing actress, singing this haunting original tune on the Christmas episode of 90’s TV sensation “My So-Called Life.” If you remember the episode, it’s still near-impossible to hear the song without tearing up.

Boston, “God Rest Ye Metal Gentlemen”

The band Boston aren’t capable of sounding like anything but Boston, even when playing a Christmas carol. This instrumental version, released online in 2013, features plenty of soaring guitar work and big, grandiose drumming.

Letters to Cleo, “Christmas Song”

The beloved Boston band did a full Christmas EP in 2019, but this track comes from their earlier days. Kay Hanley delivers one of her most attitudinal vocals, as she asks the question on everybody’s mind: “Where the (expletive) are my presents?”

Erin Harpe & the Delta Swingers: “Drink and Get Drunk”

The local blueswoman does love the bawdier tunes, and this one (from her splendid Christmas Swing album) imagines a holiday romance fueled by whiskey and gin. Just stay sober enough to appreciate her tasty, Delta-inspired guitar work.

Cold Expectations, “Coat of Snow”

Lovely bit of shimmering pop from this current band, whose male/female chorus harmonies project wintry moodiness and hope in the distance. From 2021, but harks back to the best of ‘80s new wave.

The Peppermint Kicks, “It’s a Peppermint Christmas”

Released last year, this is a worthy addition to the local holiday canon. The Peppermint Kicks are two local MVPs — Dan Kopko (Watts, Shang Hi Los) and Sal Baglio (the Stompers), getting in touch with their classic pop roots. This tune is pure high spirits; it starts out sweet and wintery, and turns into a guitar-slinging strut.