Age 5. I was a 90's kid, so is Thomas. Cool was wearing your hat backwards and watching Batman. By those terms, I was cool, at least.

Age 13. Thomas and I both really like hats. Always have, always will.

Age 17. School takes over everything. AP classes means no social life at all. I really like the face here.

Age 25. The Thomas you all know and love, minus 1 year. Not a whole lot changed in that year.

I know it's all lineart. I didn't feel like coloring. Deal with it.
If you'd like to do this, then here's a blank one:
http://fc07.deviantart.com/fs43/f/2.....amberneely.png
This was actually kinda fun.