I chose to stick with commercials that celebrities made after they'd found fame, since it makes some of these choices more awkward. Lets review some of these flops.
Lindsay Lohan - Fornarina
I'm starting with one we all know and love. This commercial features Lindsay Lohan who has gotten stuck in a dopple (shout out to ONTD MSTies with that reference). She bounces around in front of a badly animated background just saying random words. I'm still not really sure what Fornarina is, but I'm glad it exists because this awkward commercial is gold.
Lauren Bacall - Beef
This commercial is...something. Elderly Lauren Bacall basically eye-fucking the audience trying to get them to buy beef is an odd approach, but I'm kind of obsessed. IMPROVISE.
Orson Welles - G&G Whiskey
After making Citizen Kane, one of the best movies of all time, at just 25, Welles had trouble keeping his career afloat. He made more movies and acted in many film roles, but none of them matched the success of CK. While he lived comfortably, he spent the last 15 years of his life trying to raise money to fund his comeback film, and he did this by reluctantly promoting products. Maybe that's what makes this G&G Whiskey commercial so sad and uncomfortable. You can tell he doesn't want to be doing this, he doesn't want to be there, and he's about to jump out of the chair, grab his check and leave. This Japanese commercial inspired Bill Murray's character in Lost in Translation.
Jamie Lee Curtis - Activia
I'm sure we're all familiar with the Activia commericals featuring Jamie Lee Curtis raving about how much better she's pooping now that she eats this sugar-filled yogurt. We're happy for you Jamie, but enough girl.
Mr. T - Flavorwave Oven
This one's kind of cheating because it's an infomercial, but boy is it awkward. Mr. T enters the traditional infomercial kitchen set by busting down the door, and is greeted by the applause of about 100 elderly women. It's pretty amazing.
Kris Jenner - Zestra
Probably not surprising to see the matriarch of oversharing talking about how much she loves lube, but no one asked for it.
Bob Dole - Viagra
While Viagra might be a household name today, in the late 90s they were trying to put the word out, and who better to promote the product than...former presidential candidate Bob Dole? Hearing Bob Dole talk about getting hard is still super awkward 20 years later.
Source: 1, 2, 3, 4, 5, 6, 7, 8
Best/worst celebrity commercials?