Definitely Naruto himself. He has such a vibrant and unique personality. His never - give - up attitude would make him an amazing Pokemon trainer. He would approach Pokemon battles with the same tenacity he has in ninja battles. Also, his ability to form strong bonds, like he did with his friends in the Leaf Village, would translate well into bonding with his Pokemon.
Sasuke could be a very interesting character in this crossover. He has his own dark and brooding nature. He might be more interested in the stronger and rarer Pokemon. His sharingan could give him an edge in understanding Pokemon's abilities and behaviors. He could also train Pokemon in a more intense and strict way compared to other trainers.
Arceus would likely be the most powerful in terms of pure Pokemon power. It's a god - like Pokemon with the ability to create the entire Pokemon universe. However, if we consider Naruto characters as well, Naruto in his Six Paths Sage Mode could be extremely powerful. He has access to vast amounts of chakra and can perform incredibly powerful jutsus. If he were to team up with Arceus, they would be an unbeatable force.
War from Darksiders could also be a great crossover character. His brute strength and his weapon skills would be a contrast to the ninja in the Naruto world. He could be sent to the Naruto world on a mission and end up getting involved in the conflicts between the ninja villages. His war - like nature might make him either a feared or respected figure among the ninjas.
Sailor Moon and Naruto would be a really interesting pairing. Sailor Moon is all about love and hope, while Naruto is full of determination and grit. They could learn a lot from each other. Another interesting pairing could be Sailor Mars and Sasuke. Sailor Mars has her fire - based powers and a strong will, and Sasuke has his Sharingan and his own complex personality. Their interactions could be full of tension and growth.
Naruto and Sailor Moon would be an interesting pairing. Naruto's brash and head - strong nature combined with Sailor Moon's kind and gentle yet determined personality could lead to some great character development moments. They could learn from each other's ways of handling difficult situations, whether it's Naruto's battles against powerful ninjas or Sailor Moon's fights against the forces of evil.
Goku from Dragon Ball (just kidding, not part of Naruto or Pokemon but for a fun comparison). Seriously, Kakashi would be great. His laid - back but highly skilled nature could make for some interesting interactions. He might have a team of unique and rare Pokemon that he's collected over the years. And his experience as a ninja teacher could also come in handy when training Pokemon. He could teach them ninja - like stealth and combat maneuvers.
Naruto would be the most interesting. His energetic and head - strong personality would make for great interactions with the Pokemon world. He could be constantly amazed by the different Pokemon and their abilities, yet still use his ninja skills and quick thinking to adapt. His ability to make friends easily would also mean he'd quickly bond with his Pokemon and other trainers.
I think Naruto himself would be very interesting. His energetic and fearless personality would contrast greatly with the spooky atmosphere of Sleepy Hollow. He would likely approach the strange happenings in Sleepy Hollow with his usual enthusiasm and determination to overcome any challenges.
Definitely Naruto himself. His positive attitude and never - give - up spirit would contrast greatly with the more morally ambiguous characters in Highschool DxD. He could also introduce the concept of chakra and ninja techniques, which would be completely new to the Highschool DxD world. His rasengan, for example, would be a very powerful and unique ability in that universe.
Eleven could also be a great crossover character. Her telekinetic powers are very different from the abilities in the Naruto universe. If she were to be in the Naruto world, she could learn about chakra and perhaps find new ways to use her powers, or vice versa in the Stranger Things world where Naruto characters show up.