I am in the process of converting a a friend to being a "wrasslin" fan. It is not an easy task, but we have an agreement that I will not judge Tyler Perry's Madea movies until I watch one and he will not judge "wrasslin" until we watch two Royal Rumble PPV's (Pay-Per-View). I picked the Royal Rumble for a reason because it is the best way to introduce a fan to wrestling.
First off, you cannot have someones first PPV be any of the other big four PPV's. Wrestlemania has too many big storylines coming to a finish at it's annual event. The storylines are in their season finale phase and trying to explain every storyline and how it led up to Wrestlemania. The same applies to Summerslam so don't have them watch that. Survivor Series is too gimmick based for someone to properly understand what is actually going on story wise.
Now I can hear some of you say "Cleveland, The royal rumble is one big gimmick, you stupid idiot." Fair point, Chris Jericho fair point indeed. That being said, the Rumble's gimmick is so simple to understand that it not being a traditional match doesn't take away from it's entertainment value. People enter, and your only eliminated if your thrown over the top rope and both feet hit the floor. That is so simple yet entertaining to watch.
A big point about the Royal Rumble is that the surprise appearance of 30 different wrestlers adds to the energy taken from the PPV. The audience audibly reacting to every entrant, good or bad, is a thing of beauty and is done 30 times across the hour long PPV. The rush of the music hitting and watching people bear down on the ring is some thing even non wrestling fans can appreciate for the visual alone. The final beauty is that you can explain every person 1 by 1 to your friend because it takes people time to get to the ring. You can amply explain most characters in the relatively short time it takes them to get to the ring and not innundate your friend with info.