Hollywood? More like Holly's dating WHO?! Tinseltown brings together some of the most... erm... eccentric folk from around the world. So with all that energy clustered into one space, sparks are bound to fly, right? Even if they're sorta sparks you'd never, EVER imagine to fly... Like, the most random sparks you wouldn't conjure up in your wildest dreams, LOLz! Related: Celeb Couples With The Biggest Age Gaps But hey, opposites attract! And this list of The Most Random Celebrity Couples is proof! Starting off, we have.. Contents [hide] 1 Kim Kardashian & Pete Davidson 2 Sydney Sweeney & Scooter Braun 3 Gwen Stefani & Blake Shelton 4 Tyga & Avril Lavigne 5 Chelsea Handler & 50 Cent 6 Bill Murray & Kelis 7 Brigitte Nielsen & Flavor Flav 8 Kylie Jenner & Timothée Chalamet 9 Cher & Alexander "AE" Edwards 10 Scarlett Johansson & Jack Antonoff Kim Kardashian & Pete Davidson (c) MEGA/WENN Kicking off our list, we present you a couple that shocked EVERYONE when they first hooked up: Kim Kardashian and Pete Davidson! No one would have ever paired this couple - Kim, a 40s-something mother-of-four fresh off a divorce from Kanye West who's built a whole EMPIRE on looking perfect, and Pete, a 20s-something stand up comedian with a proclivity for the high life and raunchy jokes. While their relationship didn't even end up lasting a full year, it was enough to shock the globe. But NO one was more upset about it than Ye! Ha! Sydney Sweeney & Scooter Braun (c) MEGA/WENN When ranking hot button couples, we'd be remiss to mention Sydney Sweeney and Scooter Braun! They're literally two of the most controversial figures in Hollywood today, so when fans found out they'd come together, it was open season in the roasting department! Who would have expected Sydney - who broke off an engagement this year and has widely been linked to Glen Powell - would end up dating the dude who sold off all Taylor Swift's master recordings?? Not us! Gwen Stefani & Blake Shelton (c) WENN/Avalon OK, if we're talking random celeb couples, there's no WAY we could leave Gwen Stefani and Blake Shelton off the list. We mean, who would have ever thought the artist who sings Just A Girl, known for her signature punk style, would go on to date AND MARRY the guy who sings God's Country?? We don't know what's more random - the fact that they got together in the first place, or the fact that it wasn't just a smash and pass! View this post on Instagram A post shared by Gwen Stefani (@gwenstefani) Tyga & Avril Lavigne (c) MEGA/WENN If we're talking punk princesses, we can't go without naming Avril Lavigne. Who would have EVER thought she'd go on to date Kylie Jenner's ex, rapper and OnlyFans model Tyga??? The pairing just seemed SO out of left field when romance rumors first flew in early 2023! But we all know opposites attract... And as she once sang in Sk8er Boi, "He was a boy, she was a girl. Can I make it anymore obvious?" We guess it really is that simple! But while they may have burned bright for several months, the artists ultimately called things off for good in October of that same year. You just had to be there! Chelsea Handler & 50 Cent (c) MEGA/WENN At the height of Chelsea Handler's talk show success in 2009, she managed to land one of the hottest rappers at the time for a chat: 50 Cent. And at the time, their chemistry was VERY apparent! We mean, just ch-ch-check out this clip (below): And two years later, the pair made things official! Well, somewhat official. They mostly kept things casual until things eventually fizzled out, but Chelsea still to this day has nothing but nice things to say about the Candy Shop rapper. In 2020, she even dedicated an Instagram post to her "favorite ex." HA! See (below): View this post on Instagram A post shared by Chelsea Handler (@chelseahandler) And during an appearance on the Call Her Daddy podcast earlier this year, she gushed: "He was beautiful, he was a sweetheart, he was so sweet. " Very cute! Bill Murray & Kelis (c) Kelis/Instagram/MEGA/WENN Bill Murray and Kellis are not only a random pairing, but also ripe for another famous list of ours: Celeb Couples With The Biggest Age Gaps! No one expected the 75-year-old actor to sweep the 46-year-old singer-songwriter off her feet, but that's exactly what he did! Or, that's at least what a lot of people believe. The rumors came pouring in in 2023 when the unlikely pair were spotted hanging out, but by the end of summer, sources claimed the Milkshake singer dumped the Ghostbusters star. Neither ever really publicly addressed the alleged romantic fling... until earlier this year! In March, Bill kinda-sorta denied they were ever actually together to begin with. He claimed on SiriusXM's Sway in the Morning: "I met this girl named Kelis. I got great press that I was dating her. That really raised my cred a lot." LOLz! Random for sure! Brigitte Nielsen & Flavor Flav (c) PNP/WENN Next, we present you with some straight up reality TV royalty: Brigitte Nielsen and Flavor Flav! The Da