Raised on Rosie O’Donnell Christmas

By Lyndsie Kiebert-Carey
Reader Staff

The Rosie O’Donnell of my childhood made Christmas music.

I think her role in the 1992 film A League of Their Own existed somewhere in the recesses of my mind, but her comedic and talk-show-host stardom were not on my radar in any major way during my early youth. Her 1999 and 2000 Christmas albums — titled A Rosie Christmas and Another Rosie Christmas, respectively — were, however, a staple of my family’s annual holiday traditions.

I confirmed with my mom while writing this article that she did, in fact, purchase the CDs herself. She did, she said, because she thought they’d be “fun.” 

That is one descriptor I think we can safely say still applies to these Christmas songs, which succeed thanks to O’Donnell’s humor and ability to attract some of the biggest musical talent of the preceding decades. Cher, Billy Joel, Celine Dione, Sugar Ray and Smash Mouth only scratch the surface of the collaborations, which feature both classic and original Christmas tunes.

Listening now, many of the songs hold up. We used to mock my notoriously naughty little sister with the song “Nuttin’ For Christmas,” while “Merry Christmas From The Family” — a live rendition featuring The Chicks — is the kind of hokey hillbilly holiday song that kids from North Idaho enjoy. A well-produced track titled “I’m Gonna E-Mail Santa” was truly cutting-edge for its time.

Still, I can’t help but laugh at O’Donnell’s absolute audacity at certain points on both albums. In “White Christmas,” Sir Elton John himself belts the first several verses until O’Donnell enters with her flat, timid vocals. I’m not sure whose idea it was to layer a drum machine over audio of O’Donnell and Sesame Street character Elmo talking between verses of “Do You Hear What I Hear,” but the results are equal parts creepy and endearing.

Traditional reviews of A Rosie Christmas and Another Rosie Christmas are not readily available online. Amazon reviews are, by and large, positive, with many listeners expressing shock. If I hadn’t been indoctrinated so early in life, I might be shocked at the albums’ collective excellence as well.

But, as it stands, Rosie O’Donnell’s Christmas albums are a staple of my early life. They informed my understanding of holiday music right around the time that I decided “Hey Ya!” By OutKast was the greatest song ever written (a small piece of me still believes this). 

Despite O’Donnell’s reputation as a problematic loose cannon in recent years, there’s no disputing that her all-American, funny gal demeanor at the start of new millenia worked for her — at least well enough to attract world-renowned musical talent for two Christmas albums. I also believe her intentions were pure.

At the top of her version of “Little Drummer Boy,” a distinctly R&B number featuring Ms. Lauryn Hill, O’Donnell offers a monologue.

“This record is for all the kids out there who dream of a life better than the one they’re living now,” she states as a groovy drumline kicks in. “May God grant you the strength to know it gets better as you go on. You gotta believe in yourself and know that life is a great thing. Cherish it, and you, and God. Stay positive.” 

The cringe is real, but so is the sincerity. As a kid with a good life living in a largely agnostic household, I didn’t identify with O’Donnell’s words in a literal sense, but the human desire to create and share something that might spread some hope and joy came across clear as a bluebird winter day.

That, combined with the pure fun achieved with each album, perfectly reflect what Christmas means to me.

Those willing to give Rosie O’Donnell’s Christmas albums a try can find them on Spotify.