Hat's Entertainment

Hat's Entertainment is an unmarked quest in Fallout: New Vegas.

Walkthrough
Apparently, the original draft of Debt Collector ended after returning the three tabs to Francine Garret. As such, the Fallout: New Vegas Official Game Guide lists the second part of the quest as its own, separate unmarked quest.

Go to the Strip to find Caleb near the outside of Gomorrah and initiate conversation with him. You have two choices:
 * With a Speech check of 40, you can simply ask for his hat, and he will give it up. Turn in the hat to Francine to complete the quest and gain his room key as a reward.
 * Tell him that you are a collector for the Garrets and ask him to hand over the hat. He'll respond negatively and start combat. Take his hat off his corpse and return to Francine to claim your reward.