Charmed lives aren’t actually charming. They’re defined by how much sex ordinary-looking dudes can have with hot women. It’s not the only measurement of quality of life, but it’s the best one. Friendships are probably a distant second. To confirm this ranking, ask your best friend if he’d sell you out for one night with a Victoria’s Secret Angel. Or don’t bother, you know the answer.
We’re used to seeing Hollywood strong-jaws like Clooney, DiCaprio, and Pitt, pulling down tons of hot model and actress tail during their prime hunting years. Nobody understands trigonometry. Everybody understands why the barely-legal Lithuanian model is hooking up with Leo. Handsome, rich, successful dudes attract upwardly mobile women in the same magnitude as Black Friday sales on hairdryers do to women with no practical upward aspirations. The least attractive wife or girlfriend of a premiere pro athlete was still the hottest girl at her high school. (Patrick Mahomes’ fiancee exception in play here. Don’t hate me for being the last honest man.)
Good-looking women often say they want a man who makes them laugh, but I’ve spent an inordinate amount of time with professional models and every single one of them was dating a boring, unfunny, handsome rich mope. Usually an abusive athlete boyfriend. It’s not that hot women don’t want to laugh, it’s that having to pay your own rent when you’ve got amazing tits makes things less funny. Still, every now and then, an actual comedian breaks the natural laws and slips into the mix of dudes with stellar dating histories.
David Spade famously comes to mind. Tracking paparazzi photos of Spade finds him constantly in the company of smoking hot dates at Lakers games, Michelin-star restaurants, or awkwardly not taking his shirt off on beach vacations. Haters might surmise he was the gay best friend and confidante. He wasn’t. He was the luckiest short moderately funny dude in America. Maybe the world, the stats on hot pussy success are hard to find globally. It’s like Covid deaths.
Add to the charmed-life list Jason Sudeikis. Sudeikis was a goofy improv dude who landed a writing gig and later cast appearances on SNL in the early 2000s. He quickly hooked up with Kay Cannon, an attractive comedy writer (by comedy writer standards) who set him up on his big break on 30 Rock as Floyd, Liz Lemon’s erstwhile Cleveland boyfriend. Sudeikis and Cannon divorced in time for 2011, Sudeikis’ big year. Sudeikis landed his breakout role in Horrible Bosses and bedded Eva Mendes and January Jones in the same annum. That’s a Brady-type Super Bowl year. His hookup with Jones went on for six months; his relationship with Eva Mendes is often referred to as “an encounter”, which if you’re a dude is about the best possible outcome you can hope for.
Sudeikis ditched them all for Olivia Wilde. She’s not just hot and a former O.C. cast member, she comes from an aristocratic British lineage, which may not mean much in the sack, but it does when you’re bragging to your buddies or one day telling your grandson who isn’t interested and probably 7, but fuck, you need to tell somebody before you go. Also, Wilde banged Ryan Gosling, Justin Timberlake, and Bradley Cooper in the same year, which kind of makes you pussy royalty. It’s a resume builder for certain.
Sudeikis stuck with Wilde, did the forever engaged thing, made some kids, then split in time for Ted Lasso, the Apple TV comedy that is incredibly not good or not bad, so people watch it because you got sucked into $8 a month and there’s literally nothing else. He’s winning lots of awards. Because everybody loves him. He’s like Norm from Cheers; not surprising since George Wendt also happens to be his uncle. But he’s won more than some Emmy’s, he’s taken home Keeley Hazell, the British actress who plays the hot soccer WAG “Bex” on the show. She also had a role in Horrible Bosses II back in 2016.
Sudeikis and Hazell have gone public with their new relationship. Which essentially means he’s been forced to get dressed and take her out to dinner after they have sex. Still a fair deal overall. Hazell became famous as a late teen in the U.K. winning the Page 3 Idol contest for Britain’s hottest teen with big tits willing to bare them in a tabloid. (See her stellar topless Thailand bikini shoot video.) It’s not like winning the title in L.A., but it’s still something. She went on to do a bunch of topless and bikini modeling into her early 20’s before going legit with bit entertainment roles. She’s now ensconced firmly in the lap of the climb, bedding the eponymous lead star of an Apple TV hit show. At 35, it’s past prime time in this market. Hold on not so loosely.
As for Sudeikis, maybe this is the big fireworks end of the run for him. The thing about guys like Clooney, even aging, they still look like guys like Clooney. Sudeikis is quickly gelling into the guy who’s way too old to be bagging groceries you’re pretty certain did time for something creepy. The mustache doesn’t help. But for the time being, give credit where credit is due. When a man plays way above his league, we all win. Though only he gets the prize.
