I think Naruto and Dante would be an interesting pairing. Naruto's positive and determined attitude would contrast with Dante's more laid - back but still badass demeanor. They could learn a lot from each other in combat. Another interesting pairing could be Sasuke and Vergil. Both are brooding characters with a thirst for power, and their meeting could lead to some intense power struggles or even a begrudging mutual respect.
Ruby and Dante would be an interesting pairing. Ruby with her innocent and positive attitude could contrast with Dante's more laid - back and devil - may - care nature. They both are great leaders in their own ways and could learn a lot from each other in combat. Dante could show Ruby some new sword techniques and Ruby could show Dante the power of Aura and how it can be used in battle.
Trish could be the most interesting. She has a complex past being a demon created by Mundus. Her alluring appearance and her powerful demon - like abilities make her stand out. In a fanfiction with Naruto, she could be the one who is more open to learning about Naruto's world and his powers. She might see in Naruto a chance to break free from her past and the expectations placed on her in the Devil May Cry world. Her relationship with Lady could also be further explored as they both interact with Naruto, and she could be the one to initiate the idea of a deeper connection with Naruto, whether it's a true'mate' relationship or just a strong friendship.
Naruto and Lion - O would be an interesting pairing. Naruto is full of energy and determination, and Lion - O is a noble leader. They could learn from each other's leadership styles. Naruto could show Lion - O how to inspire through his own brand of perseverance, and Lion - O could teach Naruto about the responsibilities of being a true leader. Another interesting pairing would be Sakura and Cheetara. Sakura has her medical ninjutsu skills and combat abilities, while Cheetara is fast and agile. They could train together and exchange fighting techniques.
Naruto and the Penguin would be an interesting pairing. Naruto's naivete and Penguin's deviousness would create a great contrast. Naruto might try to reform Penguin, seeing the good in him, while Penguin would be constantly plotting against Naruto, creating a lot of comical and tense situations.
I think Kakashi and Riddick would make an interesting pair. Kakashi is a highly skilled ninja with a lot of wisdom, and Riddick has his own set of skills and street - smart knowledge. They could exchange ideas about combat strategies. Also, Hinata and Riddick could be an unexpected but interesting pairing. Hinata's gentle and shy nature could be a foil to Riddick's rough exterior, and she might be able to show him a different way of looking at things in the Naruto world.
Definitely Naruto and Iron Man. Naruto is this energetic, determined ninja, and Iron Man is this brilliant, sarcastic inventor. Their personalities are so different yet they could learn a lot from each other. Iron Man could be intrigued by Naruto's chakra system and try to replicate it in some way, while Naruto would be fascinated by all of Iron Man's high - tech gadgets.
Another great pairing would be Sasuke and Wolverine. They both have a dark and brooding side. Wolverine's regenerative abilities and his adamantium claws could be compared to Sasuke's Sharingan and his various ninja weapons. They might start off as rivals, but eventually come to respect each other's skills in combat. Also, they could both share stories about their past traumas and how they overcame them to become the strong fighters they are today.
One interesting pairing could be Naruto and Huey Freeman. Naruto's naivete and idealism could be contrasted with Huey's more politically aware and cynical nature. They could learn a great deal from each other. Naruto might teach Huey about the power of believing in oneself and never giving up, while Huey could introduce Naruto to the complex world of social and racial politics.
Naruto and Timmy Turner could be an interesting pairing. Naruto is all about achieving his dreams through hard work and determination, while Timmy has his fairy godparents to grant his wishes. They could learn a lot from each other. Naruto could teach Timmy about perseverance, and Timmy could show Naruto the power of imagination.
Naruto and Rukia could be an interesting pairing. Naruto's exuberant and positive personality could contrast with Rukia's more reserved and serious nature. They could learn a lot from each other. For example, Naruto could teach Rukia about the importance of never giving up and believing in oneself, while Rukia could show Naruto the more disciplined way of the Soul Reapers.