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Richie Tozier is doing pretty well, as far as the Losers are concerned. Dude has a nice home life, a nice group of friends (even before the Losers band together), and a bunch of interests.
Top of the list of interests is doing his voices: fairly terrible impersonations of various caricatures. (And, yeah: a bunch of them are offensive. It was written in 1986 and…it often shows.)
These voices are half of the reason that Richie is known as Trashmouth. The other half is that Richie really, really suffers from verbal diarrhea. He talks back to teachers, movie theater usher, and bullies. And he has the broken glasses to prove it.
His role as a member of the Losers is cathartic: he functions both as a near-permanent distraction and as a catalyst for action. When the Losers are worried sick about sharing real estate with a homicidal clown, Richie is there to crack a joke. When the Losers are poised to act—like, say, check out the spooky house on Neibolt Street where Eddie saw a leper—Richie pushes them along.
The most pertinent manifestation of Richie comes at the end of a very convivial reunion meal between the adult Losers. It's a Chinese restaurant, and the lunch is finished with fortune cookies.
Unfortunately, It has gotten into the fortune cookie batter. Each Loser cracks open something personally terrifying—Beverly's cookie is full of, you got it, blood. Richie has an eyeball.
This eyeball has its genesis in a scary movie Richie saw that featured a huge, sentient eyeball. But it also reflects back on to what Richie sees as his weakness: his eyesight is pretty terrible, and he wears thick glasses. He's well aware that a bully (or a murder clown) could undo him just by swatting his specs to the ground.
Perhaps as a result of his poor eyesight, Richie makes the world of sound his domain. He ends up a wildly famous DJ, renowned not only for his voices—which have gotten pretty insanely good by the time he reaches his mid-thirties—but also for his DJ skills.
Richie's adult life is perhaps the most glamorous of the Losers: it's a slightly tacky parade of Los Angeles-based celebrities, music, good suits, and networking. We think that's fitting for this goofy but good-natured clown.