This one should be interesting.
I think it's going to be important to emphasize one thing with this: We are evaluating the women IN THEIR PRIME.
Granted, let's be fair: Jenna's looking arguably better now ...
... then she has at times in the last 15 years ...
I'll let you decide what you consider to be when she looked her best — in Private Parts, circa 2000, when she first started, whatever — but try to evaluate her at her best, not her worst. Hopefully you've all seen her stuff. Choose accordingly.
Pornstar Bracket: Madison IVY vs. Jenna JAMESON
Madison IVY
32DD-24-32
PIC: tuscl.net CLIP: (hardcore) xvideos.com
Ivy is unique. She's only 30, but has been in the business since 2007 and has bounced in and out. She was born in Germany, but raised in Texas. She's just 4'11", so her DD enhancements look even bigger on her frame. A yoga instructor and fitness trainer on the side, she can take it with her legs behind her head, and she's willing to do so in either spot down there. Ivy's no stranger to men, but she's been in a relationship with another female pornstar, Heather Starlet, since 2013. Ivy's stuff often sees her going glamorous, but her flexibility and vast array of possible positions is what sets her apart. If you don't know her well, you should.
Jenna JAMESON
32DD-22-33 (these have fluctuated)
PIC: tuscl.net CLIP: (solo strip) pornhub.com
Simply put, the Queen of Porn. In the 90's, and for a healthy chunk of the 2000's, no one was better at doing it on camera, or maybe just doing it, than Jameson. What made her so sexy? She didn't necessarily have as pretty a face as the Playboy models of the time, and while she had a killer body, that didn't set her apart. In my opinion, it was her eyes, specifically the sexy look she would give while doing her business. Jameson's come-hither stare was epic, on par with mainstream legends like Marilyn Monroe. She also recognized that being sexy didn't stop once the sex started. Yes, things have been weird for her since the mid-2000's. But when she was at her best, no one was better.
I've made my plea for how you should look at it. I leave it in your hands.
IVY JAMESON or NEITHER


NEITHER