Ultimate Pittsburgh Holiday Mixtape: Festive tunes with local history | Holiday Guide | Pittsburgh | Pittsburgh City Paper

Ultimate Pittsburgh Holiday Mixtape: Festive tunes with local history

Listening to Christmas music is arguably the best way to get yourself into the holiday spirit. There are quite a few songs to choose from, so let us take some of the pressure off and recommend these tunes by Pittsburgh-based artists (or composers). We even reached out to some of our favorite local DJs and radio personalities to get suggestions. Happy Holidays!

“Have Yourself a Merry Little Christmas” - Lena Horne

Lena Horne spent some of her formative music-making years in Pittsburgh, so listen to this song by a music legend and honorary Pittsburgher.

“Silver Bells” - Dean Martin

“Silver Bells” was technically written by Pittsburgh composer Jay Livingston, so any rendition of it would qualify as a Pittsburgh holiday song. Martin’s classic vocals give this song a smooth and relaxing feel. It was the obvious choice.

“Please Come Home for Christmas” - Chris Jamison

Chris Jamison is a Pittsburgh-born musician best known for his stint on season seven of the singing competition show, The Voice. He delivers a soulful version of this classic song, originally released in 1960 by American blues singer and pianist Charles Brown.

“Christmas Eve” - Billy Eckstine

The late Billy Eckstine is an American jazz and pop singer from Pittsburgh who is best known for his work as a jazz vocalist who traveled across America with his own big band. His band became a sort-of finishing school for some jazz greats including Dizzy Gillespie, Miles Davis, and Sarah Vaughan.

“Sleigh Ride” - Thea Austin

Best known for her 1992 dance hit “Rhythm is a Dancer,” which she wrote and sang for the group Snap!, Pittsburgh-born Thea Austin also released “Sleigh Ride” on her album Christmas with Thea.

“O Holy Night” - Billy Porter

While Billy Porter, born and raised in Pittsburgh, has been taking over the acting world, he also maintains a music career that includes this beautiful version of “O Holy Night.” He also recently released his own version of “Have Yourself a Merry Little Christmas.”

“Dearest Santa” - Bobby Vinton

“Dearest Santa” may not be the most well-known holiday song, but this one by Canonsburg’s Bobby Vinton is sure to put you in the holiday mood.

From Liz Felix at WYEP:

“That Spirit of Christmas” - Anton DeFade & Clinton Clegg

Two members of The Commonheart recreate the Ray Charles ballad from National Lampoon's Christmas Vacation, complete with horns!

JM the Poet, Livefromthecity, and Jordan Montgomery - “Santa Got Jacked”

Pick up the holiday tempo with this song from three of Pittsburgh's best rappers.

From DJ Arie Cole:

“Winter Song” - Clara Kent

Clara Kent's Winter Song is a beautiful ballad and change of pace from the traditional cheariness of holiday tracks. I love this song because this season can be tough for a lot of people. This track gives you the space to be in your feelings while enjoying a very melodic vibe.

From Mike Canton at WYEP:

“Aguinaldo” - Geña, Miguel and Phat Man Dee

If I have total freedom, I pick “Aguinaldo,” by Geña, Miguel and Phat Man Dee. “Aguinaldo” is a staple of my annual holiday special because it captures the Latin tradition in such a joyous way.

From Ally Bear at KISS:

“Christmas Time” - Christina Aguilera

I'm choosing “Christmas Time” by Christina Aguilera (who grew up in Wexford). I love a good '90s bop, especially at Christmastime. The song is just cheesy enough and her voice, as always, sounds fantastic.