I'd take moped and flip flops guy. Rolex and wanky suit guy sounds... well... wanky. :p
Ryan, you have the benefit here of many "hot girls" who are into tattoos responding to your post (at least I imagine everyone who posts on LST to be a beautiful person. Right?) Getting a tattoo is not going to make a difference. Your personality and confidence will. By all means get an awesome tattoo, but do it for yourself. That is way cooler than getting a tattoo that you perceive will make you cool in the eyes of someone else. Girls can sniff that crap out really easily, and it is a huge turn off. No-one likes a try hard. Being true to yourself and being comfortable in your own skin is attractive.
Anyway, in response to what you actually asked... phoenix? Classic subject, awesome to look at, carries the sentiment of the quote without being a quote...