Tomb Raider is probably one of the most well known franchise due to the main protagonist Lara Craft. The series has released a certain amount of games the past few years. Believe or not when I first heard of the series, I thought it was just a movie franchise. Sometime within the past few years, I found out it was the a video game franchise. On top of that, I never played a single Tomb Raider game ever. I'm getting interested in the series but I'm still not sure where to start playing Tomb Raider.

Should I start from the first era, the second era or just wait for the reboot to come out sometime next year?

I think the more recent ones are pretty okay. I wouldn't play them back-to-back (like I did) because they are very similar. I think the older games would just frustrate most people today. I don't remember them controlling the greatest.

I'd say pick up a copy of Tomb Raider Legend (you can get a copy of that now for the change in your pocket) and is not bad at all.

Also I'd recommend Lara Croft and the Guardian of Light XBLA game. Yes it's strictly speaking not a proper Tomb Raider game, but it fun as hell if you can convince a buddy to pick it up as well.