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.
I think Vergil and Pennywise could also be an interesting combination. Vergil is very much about power and control. He would likely approach Pennywise with a more calculated mindset. Pennywise, on the other hand, would try to break Vergil's stoicism by getting into his head and exploiting his fears. It would be a battle of wills, with Vergil trying to cut through Pennywise's illusions and Pennywise trying to make Vergil doubt himself.
It's hard to say for sure, but Dante has a lot of experience and a wide array of powerful weapons and abilities. He has his Rebellion sword, Ebony and Ivory guns, and his devil trigger form which gives him enhanced strength, speed, and durability. However, Devilman also has his own unique powers, being part - human and part - devil. His ability to blend in with humans while having devil - like strength could give him an edge in certain situations.
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.
Another great pairing could be Sasuke and Griffith. They both have a certain level of ambition and a thirst for power. They might start off as rivals, constantly trying to one - up each other in terms of strength and influence. But as they face greater threats together, they could learn to respect each other and even form an uneasy alliance. It would be fascinating to see how their different motives play out when they are forced to work together.
I think Spyro and Kakashi would be an interesting pair. Kakashi is a very experienced and intelligent ninja, and Spyro is a powerful dragon with unique abilities. Kakashi could be intrigued by Spyro's magic and his different combat style. And Spyro could be in awe of Kakashi's Sharingan and his vast knowledge of ninjutsu. Also, Spyro and Sakura could be a good pair. Sakura has grown into a strong kunoichi, and Spyro could help her further develop her combat skills, especially in terms of using her strength in more creative ways.
I think Naruto and Integra would be a fascinating pairing. Integra is a strong and authoritative leader in the Hellsing world, and Naruto has his own leadership qualities within his ninja team. They could have some really interesting discussions about leadership, duty, and protecting their respective worlds. Also, Kakashi and Alucard would be a cool pair. Kakashi is known for his calm and collected nature, and Alucard's unpredictable and powerful presence would create a great dynamic. They could exchange knowledge about combat techniques and strategies from their different worlds.
Naruto and Frisk would be really interesting. Naruto is all about never giving up and has a strong sense of justice, while Frisk is determined in their own way, always choosing the path of peace and kindness in Undertale. Their combined determination could lead to some great adventures and they could learn a lot from each other's ways of dealing with challenges.
Naruto and Aang would be a great pairing. They both have a lot of similarities. They're both young heroes with a strong sense of justice and a big heart. They could learn a lot from each other's cultures and ways of fighting.
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.