A holiday music playlist feat. songs that namecheck Wawa, reimagine seasonal classics, and more
From Chuck Berry, to Kylie Minogue, to Lower Merion's own Lizzy McAlpine. Our pop music critic builds you a playlist for the season.
Christmastime is here, as Vince Guaraldi and Lee Mendelson put it in the nostalgia-inducing song composed for A Charlie Brown Christmas in 1965.
The soundtrack to that TV holiday classic has been reissued this year, so it qualifies for inclusion on this playlist of the best holiday music of 2025. The 30 songs of holiday cheer — along with interludes of winter solstice melancholy — assembled on a streaming Spotify playlist are either newly recorded this year, or as with tunes by Chuck Berry and Roberta Flack, reissued in 2025.
They come from new holiday albums by Herb Alpert, Old Crow Medicine Show, Mickey Guyton, Brad Paisley, and others. Individual songs from Philly artists like Soraia, Bret Tobias Set, and Lizzy McAlpine also make an appearance. Look out for brand names such as Luke Bryan, Cher, and Gwen Stefani.
Lainey Wilson and Bing Crosby, ‘Let It Snow! Let It Snow! Let It Snow!’
The wonders of technology bring together country star Wilson and Crosby (who died in 1977) not only in song but also visually, as claymation video duet partners.
Chuck Berry, ‘Run Rudolph Run’
A holiday classic from The Chess Records Christmas Album, a terrific newly reissued compilation that includes Sonny Boy Williamson II, the Soul Stirrers, and Salem Travelers.
St. Vincent, ‘Have Yourself A Merry Little Christmas’
The sleeper holiday album of the year is the soundtrack to Oh. What. Fun., the Christmas comedy starring Michelle Pfeiffer. Annie Clark nicely renders this melancholy classic first sung by Judy Garland. The soundtrack also includes the Bird and the Bee, Weyes Blood, Madi Diaz, and Sharon Van Etten.
Old Crow Medicine Show, ‘Bethlehem, PA’
Nashville band Old Crow Medicine Show’s holiday album OCMS XMAS features 11 originals including the heart tugger “Grandpa’s Gone.” This one imagines a “little baby born in the Keystone State” in Lehigh County and also references the Phillies to set the scene. “We drove from the Poconos, three hours to see the King,” Ketch Secor sings. “Stopped off at a Wawa store to get some gifts to bring.”
Luke Bryan and Ella Langley, ‘Winter Wonderland’
American Idol’s Bryan teams with breakout star Langley on a countrified version of the 1934 song whose lyricist is Pennsylvanian Richard Bernhard Smith.
Melissa Carper, ‘Dumpster Diving on Christmas Eve’
A lighthearted country swing tune from Nebraska singer Carper about making do someway somehow when times are tough, from the excellent A Very Carper Christmas.
Jake Shimabukuro, ‘Rudolph the Red Nosed Reindeer’
A sprightly instrumental from the ukulele virtuoso’s great new Tis the Season.
Mickey Guyton, ‘It Won’t Be Christmas’
A cheery throwback ‘60s bop that’s a highlight of Feels Like Christmas, the new album by the singer who broke through to the country mainstream with her 2020 single “Black Like Me.”
Kyle M, ‘Mrs. Claus Is Getting Down’
Former Saturday Night Live cast member Kyle Mooney has a five-song holiday EP called Winter’s Wish. This low-fi romp finds Santa’s wife cutting loose while her hubby makes his rounds. Alicia Silverstone stars in the video.
Jeff Tweedy, ‘Christmas Must Be Tonight’
The Wilco leader, who released his Twilight Override triple album this year, delivers a tender version of the Robbie Robertson-penned song by the Band. Also on the Oh. What. Fun. soundtrack.
The Bret Tobias Set, ‘For Christ’s Sake’
Philly bandleader Tobias updates a blue-eyed soul Christmas song he originally recorded with the Bigger Lovers, to a yearning duet with Krista Umile.
LeAnn Rimes, ‘Rockin’ Around the Christmas Tree’
Rimes was 13 when she had her first hit with “Blue” in 1996. That’s the same age Brenda Lee was when she recorded this holiday perennial in 1958.
Soraia, “Santa Claus.”
Philly garage band Soraia, fronted by singer ZouZou Mansour, covers the Sonics of “Louie, Louie” fame on the new It’s a Wicked Cool Christmas!, the compilation curated by Underground Garage creator Steve Van Zandt.
Chaparelle and Sierra Ferrell, ‘When It Snows in Texas’
Lone Star State trio Chaparelle teams with Grammy-winning Americana singer Ferrell on this swinging new tune about a day that may never come.
Vince Guaraldi Trio, ‘Christmas Time Is Here’
The A Charlie Brown Christmas soundtrack album has been reissued on vinyl, featuring Guaraldi’s wistful piano tune.
Gwen Stefani, ‘Hot Cocoa’
This bouncy holiday pop song is on both the expanded edition of Stefani’s You Make It Feel Like Christmas album and the Oh. What. Fun. soundtrack.
Deer Tick, ‘Light Up Reindeer’
A reflective song about anxiety in the holiday season from the Providence, R.I., rock band.
Lizzy McAlpine, ‘Celebrate Me Home’
Lower Merion native and Broadway star Lizzy McAlpine’s cover of Kenny Loggins evaded my notice last year, so it’s in this 2025 mix.
Herb Alpert, ‘Sleigh Ride’
Nonagenarian music executive and bandleader Alpert plays his trumpet and sings along with his wife, Lani Hall, on one of 11 chestnuts on his new Christmas Time Is Here.
Trisha Yearwood, ‘Candy Cane Lane’
Yearwood takes a stroll down a red-and-white-striped street on her album Christmastime that’s produced by Don Was and features husband Garth Brooks.
Kylie Minogue, ‘Office Party’
A sassy new track from the Australian diva, from the new “Fully Wrapped” edition of Minogue’s 2015 Kylie Christmas album, which also includes a beyond-the-grave duet with Frank Sinatra.
Cher, ‘Christmas Is Here’
She sang “Run Rudolph Run” on SNL this month — with Roots guitarist Kirk Douglas playing Chuck Berry licks — and released a Christmas album in 2023. Now, Cher’s added this propulsive track to her Christmas song list.
Roberta Flack, ‘The Christmas Song (Chestnuts Roasting on an Open Fire)’
The elegant, soulful singer who died in February recorded this Mel Torme-penned Nat King Cole holiday classic on her 1997 The Christmas Album. It’s been reissued as Holidays.
Eric Benet, ‘I Really Don’t Want Much for Christmas’
Eric Benet puts family and romance above material things on this R&B holiday song from his new It’s Christmas album.
The SarahBanda, ‘Overture (from the Cuban Nutcracker Suite)’
Tchaikovsky hits the dance floor on Cuban Christmas, thanks to the SarahBanda, Havana musicians led by Berlin Philharmonic French horn player Sarah Willis.
Dar Williams, ‘I Want To See The Bright Lights Tonight (Santa Version)’
Folk singer Williams covers the title track to Richard and Linda Thompson’s 1974 album, updated with sleigh bells.
Tyra Banks, ‘Santa Smize, Santa Smize’
A loopy hip-hop electro banger that does double duty as a dance floor mixture of mythical North Pole lore and an ad for Banks’ hot ice cream brand.
Brad Paisley, ‘Counting Down The Days’
We could all use a break this time of the year, country singer and guitar hotshot Paisley thinks. “It’s been a grind, but I can see Christmas lights at the end of the tunnel.” From the new Snow Globe Town.
Sofia Talvik, ‘Poem at Year’s End’
Ruminative late December song from Swedish songwriter Talvik from her Wrapped in Paper holiday collection.
The Dollyrots, ‘Auld Lang Syne’
A punk-rock take on Robert Burns also on It’s a Wicked Cool Christmas!, complete with singer Kelly Ogden’s New Year’s resolutions. “Every morning we’re going to do one thing to make ourselves feel better, and then one thing to make somebody else feel better.” Cheers to that.