About 10 or so. I’ve done about everything - best man, groomsman (most frequent), usher, reader, host, and even officiated one.
Usher is my favorite role. It’s all the wedding party perks with less responsibility.
I almost always love being in weddings. Anymore, you get a new suit for cheap, and you’re at a party where you don’t pay for booze or food.
And this is why Al and I are friends.
I would guess I've been "in" 15 or so? Close to ten as a groomsman, usher in several, officiated three, and a groom in one. I (half) joke when I get to weddings I'm not in, that I'm the #1 wedding bench player and can fill in any position at any time. Almost had to do this when the preacher got caught in a snowstorm. I offer my services to officiate, but it must be people I know and love, a relationship I support, and not in a church (I'm not super religious and not going to pretend that I am).
Point on ushers is totally true. You escort people in, then have option to sit on the church steps and have a beer while you wait for the ceremony to run its course.
Only complaint is when wedding parties require you to rent a tux or buy a dress (for women). Wife and I had guys wear their own black suit (and if you don't have one, you should - for the price of renting a tux). Asked them to buy a shirt and tie that would match up the party, but practical clothes they would still wear after. Asked bridesmaids to wear an appropriate black dress. Everyone looked great, I believe, because they were more comfortable in our own clothes. Some people even thought we made the girls order different dresses. Weddings are a racket - always appreciated when the father of the groom would pick up the tux tab.