 If you liked
Golden Boy
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 ...then you might like
Gintama
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Do you like following the adventures of a chill protagonist, whose childish behavior hides his true strength and maturity? Do you enjoy comedy anime in general? Both these shows feature a man working in all sorts of occupations and missions. The shows are mostly episodic and each episode comes with it's own set of side characters that the protagonist guy has to assist in some way.
Both series have a clever humor and charismatic main characters that give the "face of series". Both are adventure, if you like one of them, you will enjoy another. This two series show how humor can really improve the show.
kentaro reminds me of gintoki. their character is bit similar. where they act like an idiot in a certain situation, But deep inside they understand people around them and help them about their problems in life. And if you're looking for the same vibe as gintama, I swear you're gonna like golden boy too. enjoy!