What's great is a lot of my favorites were already posted so lets me find a few more that couldn't make the cut otherwise. Clay Mann(my top 5 possibly could be all Clay Mann covers) and Gambit Revolution cover. All New x-factor and the infamous Remy And Rogue cover. Uncanny X-men 277. I forget which issue it is but the one Apple posted with the close up of Gambit with the 3 cards is great and Endangered Species X-men would all be in the run for me normally.
But for my 5 I think
1. Ultimate X-men
The writer of the book hated Gambit and didn't want him in the book but he took a two issue vacation and they wrote a Gambit story there. And it gave me one of my favorite covers. I'm a huge minimalist art fan. Any art that can convey a character with the least amount of details is always beautiful to me. There was also a cover for Deadpool v Gambit I was thinking about cause it was very minimalist but it just seemed repetitive of this one.
2. X-men Legacy #245
It must be the American in me but I love an AU Gambit with a gun lol "it's got a good spread"
3. X-men vs the fantastic 4
Gambit as the human torch. It's so cool