Remember the shock when these two came out as a couple? Not only was there the 18-year age difference, but we knew Evan as this fairly innocent ingenue from Thirteen, and Manson is just terrifying. And then Evan started shifting her style to look like Manson and his ex Dita Von Teese. But the two dated off-and-on for three years and even got engaged before calling it off.
Sadly, these two probably make every "bizarre couple" list, but here they have the dubious honor of the biggest age difference: Doug is 51 and Courtney's only 16. That also makes them the creepiest couple.
Remember the shock when these two came out as a couple? Not only was there the 18-year age difference, but we knew Evan as this fairly innocent ingenue from Thirteen, and Manson is just terrifying. And then Evan started shifting her style to look like Manson and his ex Dita Von Teese. But the two dated off-and-on for three years and even got engaged before calling it off.
These two aren't an odd couple so much in looks -- they're both pretty people -- as age and behavior. Sure, the 38-year-old Brian is kicking back and enjoying the profits of his Beverly Hills, 90210 fame, but we never imagined that someone like Megan would be so willing to settle down at such a young age (she's 25).
Holly had nowhere to go but up after leaving the Playboy Mansion, but this was a pretty surprising choice. Despite spending years as a Playmate, Holly has kind of a "good girl" thing going, and magician Criss Angel is channeling "bad boy." But that must be where the attraction is? Plus, the 11-year age difference must not have seemed so daunting after dating Hugh Hefner.
We will never understand what possesses 53-year-old Madonna to date such younger men: Her current squeeze is 24-year-old Brahim, and before him was then-23-year-old Jesus Luz. (And yes, she's our winner for the biggest "older woman, younger guy" age difference.)
The Doug Hutchison/Courtney Stodden of their time, but with a much more sinister twist: Woody's longtime partner Mia Farrow adopted Soon-Yi when she was 8 with her then-husband Andre Previn. Even though Mia brought Soon-Yi into Woody's family when they got together, Soon-Yi has said that she never considered Woody any sort of father figure. Thank God, since they came out as a couple when Soon-Yi was 21! They've been married for almost twenty years and adopted two kids. Shudder.
These two were likely just a one-time thing, when Tila brought the Smashing Pumpkins frontman to Bravo's A-List Awards in 2009... but they're a bizarre enough pairing (not to mention 14 years apart) that we've gotta include them.
The technology gets better, the photos get sharper, the lingerie gets skimpier, the girls change, and Hef stays the same.
