Realize I'm dating myself (but damned glad to still be alive and able to go to SXM). 1972, flying out of Dallas (Love Field)- SWA was such a rogue. If you don't know the history you should look it up.
Free Drinks! All flight attendants wore hot pants and were all runner ups for Miss Something or Other! When they said "we're leaving" you had better be buckled in, because they left!
Before I get a lot of chauvinistic responses, not saying I agree with all that. But at "twenty something" it was pretty cool.
Herb Kelleher had a pretty good idea, and his business plan was written on a napkin in a hotel bar right here in San Antonio. And it worked. I think we all have gripes about the airlines we fly - I know my own loyalties vary from trip to trip, depending on the success of the latest flight. I would embrace SWA taking a SXM route - unless I had to go half way around the country to get there. The "cattle car" tag has its reasons, but if you can save a couple hundred bucks, maybe it's worth it to MOO.