I don't dig very much, so my heartbreakers aren't really heartbreakers. they are low-value finds. These three still stick in my head, though:
1. I dug a shard to a pink BALL MASON jar in my first and only privy. It was the face of the jar, marked with BALL. Not realizing what it was at first, I threw it in a wheelbarrow with all the other shards I found there. I later found myself fratically digging for it when I realized it was pink!
2. Finding an odd GATORADE bottle on my Hillside Dump. I'd never see a glass Gatorade bottle before, so I (stupidly) decided to throw it down the hill, where it would hopefully land on the beach with my other finds. As soon as it left my hands, I regretted throwing it because I knew it would land on my other finds and shatter them. It didn't. Instead, it flew onto a boulder and exploded. I couldn't even find the cap.
3. Digging the front panel of a crude, possibly pontiled, FELLOWS CHEMISTS ST. JOSEPH. Again, this one came from the Hillside.