1. Weird Al and the Winans – In 1992 WGN ran a Christmas Special featuring/starring megahit gospel group The Winans. Seems like your typical Christmas song and dance, a few celebrities like R. Kelly and a so-young-but-so-old Edward James Olmos pop in, and a message of peace and love. And then there’s this weird thread woven throughout the special featuring Weird Al and his journey to become a true gospel singer. This whole thing is just one cringe after another.
Al shows up to the Winans’ party dressed in an awful turqoise tuxedo and ready to wow them with his gospel skills, but he comes off a little flat – according to the attendees. I thought he did just fine.
He’s advised that he needs to get his soul right if he wants to sing true gospel music, and so he’s sent out into the neighborhood to bring some street toughs in to the warmth of the celebration. All of these things are accented by Al’s exaggerated slang and posturing.
Bringing in the street toughs is not enough, so Al delivers a Christmas tree to a less fortunate family, and then for some reason is tasked with digging a hole to plant it. As he does so, a gospel choir gathers around him…
…and Al is shown the light.
He returns to the Winans’ party triumphant – dressed down as himself – and joins the gang in that timeless Christmas classic, “Go Tell It On The Mountain”.
Here’s the Al-centric bits of the special. Protip – click the settings icon and turn off annotations. Or leave them on if you don’t want to be able to see the video. Up to you. And get ready to cringe, and then get ready to cringe again. There’s no way this could have been made today.
2. Woolworth’s 1983 Christmas Ad – Presumably there was a time when circuses were looked upon favorably and this 1983 ad for Woolworth’s Christmas offerings relies heavily on that presumption. There’s not a part of this that’s not bizarre, creepy, or both. How about this guy and his popcorn popper?
Here’s the spot. It’s charming in its off-puttingness. That’s not easy to pull off.
3. Toygro Garage – Here’s an actually charming 1920s newspaper ad for the Toygro garage.
4. Betsey Wetsey – Not sure what our society’s fascination is with dolls that feel sadness and also consume food and then excrete it, but it’s not a new thing; here’s a 1950s commercial for Betsy Wetsey, the original doll who cries “real tears” and goes to the bathroom.
5. Playskool Tape Recorder – This thing certainly looks like it could go five rounds with a toddler. My eye keeps getting drawn to that oh-so-90s band-aid, though.