There are 7 Boltron messages. You need Boltron tokens to activate him, buy them from Mr Smiley or find them throughout the game, he will randomly say fortunes. So you may need more than 7 tokens to hear them all. I hear you need 50 tokens for him to give you a special bagde but I haven't done that yet.
Messages (in no particular order)
1. To tame the mighty lion, you must offer him a frozen treat. (No prize) [Lion's special ice cream treat is what you get for helping Sadie find ice.]
2. Check the prize dispenser below me! (Prize)
3. There's good times ahead in your future -- at the Funland arcade! (No prize)
4. It's dangerous to go alone. (No prize)
5. You're good looking on both the outside AND the inside. (No prize)
6. In the very near future, you will receive a special prize! (Prize)
7. Bad luck and extreme misfortune will haunt your pathetic soul for all eternity! (No prize)
Get all 7 messages and pop the achievment. I needed maybe 16 tokens to hear them all.