#2. Michael Bolton's Winning Softball
When you think of Michael Bolton, the first thing that comes to mind is mangy hair. Second is soft rock. Third is "Why?" And then, if you haven't given up on thinking about Michael Bolton yet, softball. Wait, what? It turns out, holy shit, Michael Bolton loves him some softball. Bolton's love for softball is so strong that in 2000 he recorded a 60-minute video teaching rookies the basics of the game.
"Beautiful. Let's take one more and try not to get Michael's bludgeoned victims in the shot."
Which makes us wonder, who did he think was going to watch a softball instructional video starring Michael Bolton? Real softball players? No. Horny old ladies too shy to flip the station to Cinemax? No, Matlock was still on the air.
Questionable market research aside, Michael Bolton somehow assembled a team of mulleted softball players from his band and crew. And then, because Michael was humble, he named them the Bolton Bombers. Apparently at the point of filming they had a 67-3 record, but what do you expect when your competition is the Yanni Yankees and Kenny Loggins' Kubs?
"And that's how you adjust your testicles when they get pinched in your cup."
The whole video is pretty much a gigantic wankfest, as Michael constantly reminds us how great he is, how great his team is, how great his music is and how much money he raises for charity. In fact, it seems the only thing he doesn't brag about is scoring with chicks.
One of Michael's groupies gives him her 1870s room key.
The Bolton Bombers even demolish Michael Jordan's softball team in a charity game. So if you needed another reminder about what a disaster Jordan's baseball career was, just watch him lose to Michael friggin' Bolton.
#1. The Celebrity Guide to Wine, With Steven Seagal
One of the most awkward situations in life is spending time with a wine connoisseur when you know dick-all about the subject. But not to worry, because as this 1990 video demonstrates, even celebrities can be ignorant about wine. You suddenly won't feel so bad after you see Robert friggin' Loggia offend everybody by putting ice into red wine, which causes a caterer to ... uh, have a meltdown and plow through his table.
OK, none of us wanted to be celebrities until this exact moment.
The Celebrity Guide to Wine is hosted by Bernard Erpicum, who once worked as the maitre d' at Spago in West Hollywood, a popular celebrity hangout. He obviously thought that bringing in some of his celebrity buddies would help garner more mainstream appeal for his video. No matter who those celebrities were, or whether a sane person would trust their advice on anything.
So we hear the likes of Robert Loggia, Herbie Hancock, Shelley Hack and Whoopi Goldberg deliver their thoughts on wine, and start wondering if Whoopi has a bit of a problem after she shows us the 48 bottles of wine in her trunk.
"Remember, the number one rule in wine is 'get a shitload of it.'"
To further drive home the point that even celebrities make mistakes, Dudley Moore is shown acting out an awkward and uncomfortable situation where he tries to order wine for himself and his date, and faces unbearable pressure from the snooty maitre d'. But by the end of the video, Dudley has become such an enthusiastic wine connoisseur that he can't stop talking about it. Even though having eight glasses of wine in one sitting might be a cause for concern.
Though we're sure that the best advice comes from a man whose defining role was a wealthy alcoholic man-child.
But, of course, while you're watching The Celebrity Guide to Wine, the one celebrity you just know is going to show up sooner or later is ... Steven Seagal.
"I never make major career decisions without first consulting with several bottles of wine. And a toilet."
At the time, Seagal was married to Kelly LeBrock, whom you should remember as the chick from Weird Science. It's here that the video decides to take a turn toward the erotic, as the video teases us with the promise that we might get to see LeBrock and Steven Seagal in a lovemaking session that would almost certainly involve a wine bottle in his anus. After seductively caressing the bottle for her hubby ...
... LeBrock demonstrates that the proper way to open a bottle of wine is by ... sticking it between your thighs.
"Wait, honey, show them the trick where you open it without your hands."
Seagal is clearly turned on by this, and we get this erotic exchange:
"I hope it was as good for you as it was for me."
"I have a feeling it may have even been better."
"If you need a bottle opened, you know who to call."
"Maybe I'll whistle."
Just when you think the video couldn't get any weirder, it ends with a PSA message on drunk driving delivered by ... RoboCop himself, Peter Weller:
"Excuse me, I have to go. Somewhere, there is a crime happening."
Because of course it does.
Robin Warder is the co-owner of a pop culture website called The Back Row.
For more thinks celebrities wish you didn't see, check out 8 Humiliating Japanese Ads Starring Oscar Nominees and The 10 Most Regrettable Celebrity Commercials.