Simba and Kerchak would be a fascinating pair to see interact. Kerchak is the leader of the gorilla troop and very protective. Simba is the king of the Pride Lands. They could have a bit of a power struggle at first, but then realize they both have the same goal of protecting their own and could learn from each other's leadership styles.
Tarzan and Nala would also have an interesting dynamic. Nala is strong - willed and independent. She could be both impressed and a bit skeptical of Tarzan's jungle - dwelling ways. They might compete in some skills, like hunting or climbing, and in the process, gain respect for each other.
One idea could be that Tarzan, while exploring the jungle, discovers a strange new area that leads him to the Pride Lands. There, he meets Simba and the pride. Tarzan's unique jungle skills could help Simba in some way, like teaching the lions new ways to move through the trees to escape danger. And in return, Simba could introduce Tarzan to the ways of the lions and their social structure.
I think Merida and Black Widow would be great together. Black Widow is all about stealth and combat skills in a more urban and high - tech environment. Merida, on the other hand, is used to the forests and castles. Black Widow could teach Merida about modern espionage and Merida could show Black Widow how to use the environment in a more natural, primitive way for combat and survival. They could also bond over being strong - willed women in a world dominated by men.
Definitely Joker and Makoto Yuki. Joker is the leader of the Phantom Thieves, very confident and strategic, while Makoto Yuki is a strong and silent type. Their leadership styles could clash or complement each other.
Definitely the interactions between the two versions of Leonardo. The 2012 Leo is more light - hearted in some ways compared to the very serious 2003 Leo. They could have some great moments of leadership clashes and then learning from each other. For example, the 2003 Leo could teach the 2012 Leo some of his more stoic leadership techniques.
I think the interaction between Joker (from Persona 5) and Yu (from Persona 4) would be really interesting. They are both leaders of their respective groups, so they could exchange leadership strategies and learn from each other. Also, Morgana and Teddie would be hilarious together. Morgana's serious yet sometimes clueless nature and Teddie's over - the - top and comical personality would create some great comedic moments.
The female characters like Nala and Tarzan could also have interesting interactions. Nala might be curious about Tarzan's way of life. She could ask him about the jungle, and Tarzan could be impressed by Nala's hunting skills. The other animals in the Pride Lands, such as Timon and Pumbaa, would probably be both scared and fascinated by Tarzan. They might make jokes about his strange appearance at first, but then grow to like him as he helps them with things like finding new sources of food or protecting them from danger.
The interaction between Naruto and Boomhauer could be really cool. Boomhauer has his own unique way of talking which Naruto would probably find really strange at first. But as they get to know each other, Naruto might start to understand Boomhauer's wisdom hidden behind his mumbling. And Boomhauer might be impressed by Naruto's loyalty and determination, which are traits he can respect despite Naruto being from a completely different world.
Definitely Clark Kent and Dean Winchester. Dean has his tough - guy hunter persona, while Clark is the all - American good guy with superpowers. Their different approaches to protecting people would make for some great banter and clashes of ideology. Another interesting interaction would be between Sam Winchester and Lex Luthor. Sam's intelligence and his experience with the supernatural could put him at odds with Lex's brilliant but often morally - grey mind. And Castiel and Chloe Sullivan could also have an interesting dynamic. Castiel's otherworldly nature and Chloe's inquisitive journalist side would lead to some really unique conversations.
Definitely Mario and Sans. Sans' laid - back attitude and his powerful abilities would contrast greatly with Mario's more heroic and straightforward nature. Their conversations would be filled with humor and misunderstandings. For example, Sans might make some jokes about Mario's mustache or his choice of overalls, while Mario would be confused by Sans' skeletal appearance and his knowledge of timelines.
I think the interaction between Ruby and Ben would be really interesting. Ruby is very energetic and has a strong sense of justice. Ben, with his experience of using the Omnitrix to save the day, could share some of his stories with her. They could also have some friendly competitions regarding their combat skills, like who can take down a group of Grimm faster, with Ruby using her Crescent Rose and Ben using one of his alien forms.