“Look out, everybody, things are about to get awesome!”
Once the Vault Hunter reaches the control station aboard The Handsome Jackpot, they will meet face to face with Pretty Boy, who has Timothy locked in a laser-cage near the console (close enough to it, but too far to actually reach without hurting himself). Pretty Boy will stroll closer to the character, before laughing and saying "Jackpot". At this point, The Jackpot will land from the ceiling to the ground, and grab Pretty Boy, placing him in his chest, and the fight begins.
Once the boss has its first phase ended, Jackpot will offer a critical repair in exchange for payment. Pretty Boy happily pays the fee, and the bot continues repairing while Pretty Boy calls in Loader Bots to attack. However, once the robot is downed again, it will offer a high-interest payment plan. This time, Pretty Boy will deny, only paying the original fee, and the Jackpot will accept. Once the Jackpot goes down, it will inform Pretty Boy that he has insufficient funds. It will once again offer the High-Interest Payment Plan, and Pretty Boy accepts remaking "I'll pay it all back anyway". The Jackpot will then extract a "Down-Payment", and Pretty Boy will remark about needles before screaming in pain as the Jackpot enters "Blood Cooling Mode". The Jackpot enters its final phase, but is still defeated with Pretty Boy killed from inside.
- Main article: All Bets Off
- The bot is referred to as "Jackpot the Jack's bot" in True Vault Hunter Mode and Mayhem Mode.
- Many of the Jackpot's attacks are similar to those of Iron Man in the Marvel Cinematic Universe.
- Jackpot! challenges