Honestly, the early 2000s were a fever dream. If you weren't there, it’s hard to explain the sheer chaos of MTV’s transition from music videos to "reality" spectacles. You had the Prince of Darkness living in a Beverly Hills mansion, struggling with trash cans, and a pop princess who famously couldn't tell the difference between tuna and chicken.
Then, they sang together.
It wasn't a rock anthem. It wasn't a pop ballad. Ozzy Osbourne and Jessica Simpson teamed up for a cover of "Winter Wonderland" in 2003, and it remains one of the most baffling artifacts of pop culture history.
The Christmas Special Nobody Asked For
The year was 2003. The Osbournes was a juggernaut. MTV was squeezing every drop of content out of the family, which led to The Osbourne Family Christmas Special. This wasn't your grandma's Bing Crosby special. It featured guests like Britney Spears, Rob Zombie, and, most notably, Jessica Simpson.
📖 Related: Did Bloodhound Lil Jeff Die? The Reality Behind the Chicago Rapper's Sudden Passing
At the time, Simpson was at the peak of her Newlyweds fame. She was the "it" girl of reality TV, while Ozzy was the lovable, bumbling dad who happened to be a heavy metal legend. Someone in a boardroom decided pairing them up for a duet was a stroke of genius.
Ozzy didn't agree.
Behind the scenes, the Prince of Darkness was vocal about his hatred for the project. According to reports and later reflections by the family, Ozzy was basically dragged into the studio. He famously shouted at producers, questioning why his daughter Kelly couldn't do the part instead. "Sleigh bells are you f—ing ringing, is this a joke?" he allegedly vented to Sharon.
He hated Christmas. He hated the song. But the check was likely too big to ignore.
✨ Don't miss: Fiona Facinelli College: What Most People Get Wrong About Her New Chapter
Anatomy of a Cringe-Worthy Music Video
The video for the Ozzy Osbourne and Jessica Simpson duet is a masterclass in "uncomfortable." You've got the 23-year-old Simpson in a thin slip of a dress, looking radiant and very much in her element. Beside her stands a 55-year-old Ozzy, dressed like a cross between a noir detective and someone hiding from the sun, looking like he’d rather be literally anywhere else.
The visuals are a literal interpretation of the lyrics. They build a snowman. They sled. They sit by a fire.
Why it feels so weird:
- The Snowman Incident: There’s a scene where they build a snowman, and Ozzy, being Ozzy, decides to give the snowman a "carrot dick." The look of genuine horror on Jessica's face isn't acting.
- The Sledding: At one point, Jessica—all of 100 pounds—is seen dragging a sled that Ozzy is sitting on. It looks less like a holiday frolic and more like a strange feat of strength.
- The Vocals: Jessica has a genuinely great voice for this kind of schmaltz. Ozzy... does not. His reverb-drenched "Ozzy-isms" (the "yeah yeahs" and "oh yeahs") feel like they were recorded for a different song entirely.
Tony Iommi’s "Blink and You’ll Miss It" Cameo
Perhaps the saddest part for metal fans is the appearance of Tony Iommi. Yes, the legendary Black Sabbath guitarist is in this video. He’s sitting at a piano, playing along to a pop-ified Christmas track.
He’s on screen for maybe three seconds.
It’s the ultimate "what am I doing here?" moment. For a man who practically invented the heavy metal riff, seeing him relegated to a background prop in a Jessica Simpson video is the peak of 2003 absurdity.
Why Do We Still Talk About It?
It’s been over two decades, and the internet still hasn't moved on. Why? Because it represents a time before social media was "curated." It was messy. It was authentic in its weirdness.
When Ozzy Osbourne passed away in July 2025 at the age of 76, fans didn't just share clips of "Crazy Train" or "Paranoid." They shared the "Winter Wonderland" video.
It showed a side of Ozzy that was human. He was a guy who would do something he hated because his wife and the network told him to. It was a moment of pure, unadulterated "selling out" that was so bad it circled back around to being iconic.
What You Can Learn from This Pop Culture Relic
If you're a creator or a brand, there’s actually a lesson here. Authenticity trumps perfection. This duet was objectively "bad" by almost every musical standard, yet it’s more memorable than 90% of the polished Christmas specials produced today.
- Contrast works. The "odd couple" trope is a classic for a reason.
- Leaning into the cringe. If they had tried to make it "cool," it would have been forgotten. Because it was awkward, it lived forever.
- The Power of "No." Ozzy’s reluctance is what makes it funny. Had he been happy to be there, the tension would be gone.
If you want to experience this for yourself, the video is still floating around YouTube. Just search for "Ozzy and Jessica Winter Wonderland." Be prepared to cringe, laugh, and maybe feel a little bad for Tony Iommi.
If you want to see more of the Osbourne's peak reality TV era, you can check out the archived episodes of The Osbournes on various streaming platforms to see the buildup to this legendary holiday disaster.
Next Steps:
Go watch the music video on YouTube and pay close attention to the 0:40 mark—that’s when the "snowman carrot" incident happens. You can also look up the full Osbourne Family Christmas Special on fan archives to see the Britney Spears and Rob Zombie cameos that were somehow even weirder.