Sasuke Retrieval Arc
Jirobo and three other members of the Sound Five team escorted Sasuke to Orochimaru's clutches. During there trip home, The current Sound Four ran into the Sasuke Retrieval Squad which consisted of Naruto, Shikamaru, Kiba, Akamaru, Neji, and Chouji. Thinking they were weak Jirobo decided to stay behind and take care of them. Letting the other three go on ahead. Jirobo trapped the retrieval squad in stone prison with no escape. While they were trapped Jirobo it was revealed that he was consuming their chakra.
Kiba and Akamaru used an attack called ''Fang over Fang'' to try and break out of the prison. But no avail. Shikamaru then tried to convince Jirobo to let him out and let the others stay and rot. Kiba and Naruto thought Shikamaru had turned traitor but Chouji stuck up for him, just as Shikamaru has stuck up for him all these years. Neji then explained why Shikamaru had done so, to see where there opponent was stationed. With that information Shikamaru and Neji was able to pinpoint the location of the weak spot in the trap. Chouji then used his 'Human Boulder' attack to break them out.
After they busted out, Jirobo attacked them. They barely held their own as a team. Chouji then decided to stay behind and battle Jirobo. During their battle Jirobo put Chouji down, and Shikamaru down aswell. He told Chouji that he was nothing but a pawn and that his friends never cared about him, or they wouldn't of left him behind. Chouji didn't by this and used one of his famile 'Super Food Pills' to gained speed. This caused Jirobo to go into his second stage transformation of the cursed seal, but Chouji was still no match. He then used his second pill to gain strength. Chouji and Jirobo was now on even ground. But Jirobo still proved a worthy opponent, causing Chouji to take his final pill, gaining speed, strength, and an incredible amount of Chakra. This enhanced power granted Chouji the power he needed. Jirobo was then killed in an attack by the now super-powerful Chouji.