Lupin III: Part II, City Hunter Recommendations
Both of the main characters, Lupin and Ryo, are loveable, goofy perverts who are actually really talented at other things. Ryo is great at handling a gun, while Lupin is great at stealing things.
Lupin has more of a cartoony look to it's characters, while the characters in City Hunter look somewhat realistic. Despite the differing art styles, both shows end up having a very similar tone.
In both shows, there ends up being many similar action-packed situations, which usually also somehow involve beautiful women, and the main character lusting over them / getting manipulated or tricked by them.
City Hunter and Lupin III have very similar main characters. Ryo and Lupin are both happy go lucky individuals, when it comes to business, they are at the top of their game, always seeing their mission through despite the odds.