Considering how much money there is to be made on endorsements when you're famous, it's no surprise that even the most sophisticated celebrities can be convinced to shill for brands seemingly beneath them.
Some pairings are no-brainers (athletes & athletic apparel), some are utter train-wrecks (Scarlett Johansson and Sodastream), and some...some are just plain weird. To that end, I dug up 11 of the strangest celebrity endorsements of all time, proving we all make the occasional mistake, even Bob Dylan.
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Float like a butterfly, sting like a... glue trap? Ali lent his face and tough-guy persona to help D-Con sell these innovative-at-the-time roach traps in the mid 1970s.
2. Bob Dylan - Victoria's Secret
In 2004, Dylan made a very special and very creepy cameo in a Venetian-themed Victoria's Secret ad (starring a then-23-year-old Adriana Lima). As if that wasn't weird enough, he also sings in it. Bob, what are you doing?
The country singer/songwriter, actor, and director became a quadruple-threat when he launched his very own frozen food brand, Bakersfield Biscuits. They produce easy-heat delicacies including Chicken Lickin' Chicken Rings, Lanky Links, and Macaroni Mouth Poppers. Mmm?
Amazingly, before they were dispensing vitamins that ostensibly exist to help you live, Bedrock's favorite family was in the deep pocket of big tobacco, singing the praises of their biggest sponsor, Winston Cigarettes, in a 1961 ad.
6. Mikhail Gorbachev - Pizza Hut
In 1997, the former Soviet Union leader appeared alongside his granddaugter in a 60-second commercial for Pizza Hut, specifically highlighting a particularly hot item at the time: no-crust "Edge" pizzas. He didn't personally profit from it, though. His appearance fee went directly to his non-profit.
7. Penelope Cruz - Nintendo DS
In 2012, Penelope starred in an unexpected and strange spot alongside her sister Monica for the gaming giant, in which the two play the new Super Mario Bros game against one another. After Penelope loses, she must hold up her end of a bet by suiting up like Mario—moustache and all—and head to the grocery store.
Well before his infamous Bronco ride down the freeway 20 years ago, Simpson, in an eerily prophetic move, did commercials and print ads posing as a customer who needed to score a rental car, like, really fast.
10. Ozzy Osbourne - I Can't Believe Its Not Butter
Because having a long-locked male supermodel shill for faux butter spread wasn't weird enough, they went ahead and enlisted the Black Sabbath frontman himself, alongside an impersonator to play up the comparison between real butter and ICBINB. No live animals were harmed in the filming.
11. Paris Hilton - Hardee's/Carl's Jr.
Back in 2005 at the height of her fame-for-being-famous, Hilton stripped down to her bathing suit in a commercial for the burger chain, suggestively lathering up a black Bentley while intermittently taking bites out of one of their signature beastly bunned concoctions. She later reprised her role, this time alongside swimsuit model Hannah Ferguson, in 2014, because... that's hot. I'm so sorry.
Joe McGauley is a senior editor at Supercompressor. He would buy just about anything from Penelope Cruz.