My story as a Sugita fan is a bit of a hilarious scenario: I originally became familiar with him as a seiyuu through what is arguably his most notable role, and to this day, still one of my favorites: Sakata Gintoki. Everything that has happened afterwards has been a cruel, cruel irony. I want to chalk it up to him gaining popularity around this era, but maybe some of it is simply too uncanny? I dunno... I'll let you be the judge.
"They have those stickers that say 'Merry Christmas', that you can stick on your windows, right? I like to switch the letters around and write obscene words in English."
My star sign is Pisces. There are 12 lovely zodiac signs, but guess who ended up as the seiyuu for the Pisces character in Starry Sky? Yep, it was Sugita. When the new Tokimeki Memorial GS came out, Sugita was the voice of the prince I ended up falling incredibly hard for (no matter how hard I tried not to). When Devil Summoner received a Drama CD, guess who voiced the adorable Kuzunoha Raidou who I'd loved dearly ever since playing the games? Sugita. Nearly half a decade after I read JoJo's Bizarre Adventure and declare Joseph as "Best JoJo", guess who's in the cast list as Joseph? Sugita. League of Legends finally gets a Japanese server and who voices Yasuo ~my samurai husbando~? God damn it, Sugita are you stalking me?! ಥдಥ It's like he found my list of favorite characters who didn't already have a voice and auditioned for all of them.
All the ridiculous irony aside though, I do own a gross amount of these fanlistings so I
probably definitely have some kind of gross bias. Even if I denied it any of my friends would tell you otherwise. My friends are the worst. IN MY DEFENSE, I DIDN'T MARRY CHROM IN FIRE EMBLEM ... partiallyoutofspite. To this day my friends try to bait me into fandoms with Sugita: it doesn't always work (I'm a tsundere), but I am always woefully aware of his presence in anything I get into where he's in the cast list.
Many would say that he's typecast as the "funny character" and I can't disagree with that—he's a goofy guy at heart and funny is what he excels at, and what he should be known for because he's damn good at it. However, he's been involved in many roles in his career now and I would argue against him being a one trick pony. He shows his sensitive side from time to time (the gentle Ruka and Soldier Blue) and does crazy pretty well too (holy moly, Keisuke). I think his versatility is what makes characters like Gintoki, who are so multifaceted, incredibly beautiful: he breathes life into characters because he performs so naturally on both sides of the spectrum. Aside from growing into a pretty prolific seiyuu, he's quite the class clown as well, which is what makes him so lovable as an anime industry personality. There's an embarassing amount of photos of him online crossdressing, and any other photos he's in are probably of him photo bombing someone else. One of my favorite things to watch is him and Nakamura Yuuichi on Tokyo Encounter. If you ever want to watch two grown ass men act like children and play video games, google search some episodes and you'll be in for a treat. Sugita himself is quite a character.
While I can't say that I've seen/played every single thing he's in, it's always a treat if my interests align with his voice reel... which as you can clearly see, happens more often than not. 8( Thanks for stalking MAL, Sugita.
His best role and most prolific is hands down Sakata Gintoki: watch Gintama if you’d like to see Sugita “in his element", as well as a beautiful, multi-faceted performance. (Gintoki is just as serious as he is silly.) If you're looking for something shorter but similarly silly, I also really love his performance as Hoshi in Arakawa Under the Bridge. And to just boil it down to Sugita himself: I also recommend checking out his gaming show with Nakamura Yuuichi: Tokyo Encounter. You will find watching these, that Sugita and his comedic roles are very much one and the same in terms of personality.