I've only played roulette twice. First time I bet on black eleven (for no particular reason) and I won on the first spin. I figured that wouldn't happen again, so I took the money and ran.
A few years later I was back in Calgary for a visit and out with some friends. We couldn't really agree what to do for the night, so we decided each of us would take a turn chosing something. One of my friends who was up first decided that for this turn that we would go to the casino each bet on a number in roulette and if anyone won they'd pay for the rest of the evening.
The rest of the story you can probably guess, but, anyway, I put $5 down on black eleven and sure enough it came up and I won $175 and bought drinks for the rest of the evening. It was a pretty good night
I haven't played roulette since.