1. A popular casino card game as described below, or playing roulette and letting your winning chips remain on the table in hopes of winning the same number, color, row, or any feasible bet that previously won.
2. Letting an erection stand out or be noticed in situations where one would normally try to conceal it.
A casino game popular in Las Vegas, each player receives 3 cards, and the dealer receives 2 community cards. Players can make up to 3 bets to begin, and may rescind 2 of those bets based on the strength of their hand. The game is not played "against" the dealer, per se, in order to win you generally must have at least a pair of tens.
I had two Aces in the hole, so I put up my cards in let it ride and won all 3 bets I had made.
"take it to a parade and let it ride on your shouders"
Popularized by a McDonalds commercial where two individuals go back and forth with personifying statments describing acts of endearment and special moments in order prove that the other one loves a sandwich.
As in...
Person 1: "Do you know how I know that you love that sandwich so much? Because I know you would take it to a parade and let it ride on your shoulders."
Person Two: "Oh Yeah? Do you know how I know that you love that sandwich so much? Because ..."