Jerry is a Great Khan that can't quite complete the ritual initiation to become a Khan. When Jerry was a child, the Followers of the Apocalypse came to Red Rock Canyon with pre-War books. Jerry used to spend hours reading these books, especially poetry books.
Jerry says one becomes a Khan if they survive the initiation. However, in another line he says that he has tried five times and still didn't make it. Sergeant Bitter-Root gives a different account of the Khan initiation, stating that one passes it if they can withstand the beating without yelling for mercy.
Jerry is considered a member of the Great Khans faction, even after the completion of Cry Me a River. He will therefore be hostile towards any members of the NCR faction, including those he may pass by on his journey to the Old Mormon Fort, such as the guards outside Camp McCarran and the NCR sharecroppers, as well as the gamblers being treated inside the fort itself if you actively escort him through the gate. Jerry periodically says generic Great Khan phrases.
"Her hair stands tall, like the spiky bits on a deathclaw Her eyes are bright as radioactive sludge, glowing with the light of love But when I talk to her, she laughs and mocks and has her brothers beat me Oh, why do nice girls hate me?"
Jerry the Punk is a reference to William the Bloody, aka Spike, from the television show "Buffy the Vampire Slayer". Jerry asks what rhymes with the word "indulgent", and begins to say the word "effulgent" before stopping and saying how terrible that would be. In the show, before Spike became a vampire, he was a terrible poet nicknamed "The Bloody" for his bloody awful poems. In his flashback, he is ridiculed by his peers for using the word "effulgent" in his poem. In addition, both characters wrote a love poem to a girl they loved, only to be mocked, and both characters eventually leave their homes. 
The line "Oh, why do nice girls hate me?" is a reference to Blackadder the Third, in which this line appears in a poem written by the teenaged The Right Honourable William Pitt the Younger, Prime Minister of Great Britain. 
xbox360 Jerry's pathfinding causes him to pace in the dueling ring, unfortunately this causes him to walk right past the Khans attacking the practice dummies. He will subsequently be killed and the quest will fail if the player spends too much time in the area (before or after accepting the quest). Upon the player's return, with permission for him to join the Followers, he may still be killed in this fashion, thereby rendering the quest impossible to complete if stuck in this reoccurring death loop. Jerry can be protected long enough to complete the quest by reverse pickpocketing stronger armor into his inventory. Even if he dies and after accepting the quest, Julie Farkas will still have all associated quest options in her dialog tree. [verified]
ps3xbox360 Sometimes, Jerry will not leave his tent in Red Rock Canyon once his quest is completed. He will thank the Courier if interacted with, as if he successfully made it to the Old Mormon Fort. Bumping him bodily out of the tent may start him on his way. [verified]
xbox360 After completing his quest he may be hostile if you meet him while wearing NCR armor. This may be to do with the fact that he was once almost a member of the Khans. [verified]
ps3pc Jerry may start attacking NCR affiliated gamblers inside the Mormon Fort. (This may be connected to the state of the NCR/Khans relationship at the time, per Oh My Papa). If he exits the tower the Followers guards may attack him. [verified]
[platforms tag needed] After the completion of the quest Cry Me a River, Jerry will travel from Red Rock Canyon to the Follower's base at Old Mormon Fort. Unlike most non-player characters, Jerry does not fast-travel and will only move if the player character is in the same active map cell as him. Additionally, his path takes him straight through Fiend territory, past the lairs of Violet and Cook-Cook. As he is unarmed and unarmored, he is unlikely to survive the journey unless personally escorted by the player character. Jerry can then be found inside the west tower. [verification needed]