Crowning Moment of Awesome: Winning seven Women's Championship titles, almost twice as many as the previous record (4), held by the Fabulous Moolah.
She made The Diva Search entertaining.
Her farewell match at Unforgiven 2006. The image on this page is from the post-match bows she took that night, to a standing ovation.
When she slapped on the Sharpshooter, the crowd exploded.
In December 2008, John Cena is put in a match against Santino Marella and Beth Phoenix. He spends part of the night trying to find a partner, and when he comes to the ring, he mentions that Santa left him a little gift. Cue Trish's music, and an explosion from the fans.
Cena wasn't kidding about the gift. As fans remember, Cena had a quite-obvious...erectile issue during the entirety of the match, to the point where even the commentators were audibly stifling their laughter whenever Cena (and his package) was shown close-up on camera. Apparently, Trish is that gorgeous in person.
Her retirement match deserves special mention. Pro wrestling is notorious for leaving behind a lot of wounded egos, hurt feelings, and grudges held in its wake. This is especially true for female wrestlers. However, Trish has said that her entire final match was pretty much her perfect dream match to go out on (In a later interview she said it felt like she wrote out her perfect dream match, which was then rubber-stamped without a single change made.) This sums it up.
Growing the Beard: So to speak; once she stopped being valet arm candy, and dedicated herself solely to her ring work, her popularity grew exponentially.
Most Wonderful Sound: Her laugh at the beginning of her entrance theme. It always got a massive pop.
Rescued from the Scrappy Heap: She was pretty unpopular when she started, mostly because she somehow had no charisma and was so bad in the ring that she could botch a catfight. Then there was the infamous "table promo", where she dressed up in various lingerie and writhed on some tables. Then she took a table bump from the Dudley Boys, got legitimately injured from it, and instead of quitting went through rehab and came back with significantly improved skills.
The Woobie: While she came off as a total bitch during most of her affair angle with Vince McMahon, when he started to really demean her (forcing her to act like a dog and referring to her as his "toy"), it was hard not to feel for her.
How about when she found out Chris Jericho made a bet to sleep with her? Good lord she was a convincing crier.