Yoni Wolf, the singer/rapper who leads the Cincinnati band Why?, is no fan of musical pigeon holes. “In the year 2024, I’d say that genre is a thing of the past,” he said this week. “I have eclectic tastes, and maybe I was a little ahead of my time 20 years ago. But now people feel free to go wherever they please, so I don’t feel like an oddball anymore. I mentored some kids a few years ago and was surprised and pleased at their tastes — They’d listen to grimy rap, straight pop and folk, you name it. So I think we’re getting past the idea of marketing to specific genres.”

Wolf may not be the only songwriter to blend alternative hip-hop with dreamy pop, but his work remains distinctive. Not many artists use hip-hop to convey sensitivity instead of swagger, but that’s the mood of the latest Why? record, “The Well I Fell Into,” which they’ll feature at the Sinclair Saturday. It’s a breakup-themed album that covers romantic angst in soul-baring detail.

“I call it auto-fiction. It certainly contains elements of my life in a big way. The emotional truth of my situation is in there, but a lot of liberties were taken. And that’s what I’ve always tried to do — to write what I know, whether it’s from my own life or what I’ve seen in other peoples’. A breakup will always give you a lot of feelings, and feeling yields songs. And I’m not saying you have to be miserable to write a good one, just that strong feelings always help. If I was in the Olympics and had strong feelings  about winning a gold medal, I’m sure I could get a song out of that.”

He also doesn’t mind injecting a bit of humor; not many lyricists would rhyme “blastin’” with “Ted Danson” in a rap tune. “In a record like this you can dangerously tiptoe into areas of melodrama, and I didn’t want to go that way. Unless it’s a David Lynch-ian thing, a twisted daytime television feel, which is what I was aiming for.  I’m not trying to make joke music but it helps to keep a wry smile about these things.”

Over the past two decades, Wolf has grown Why? from a bedroom-type project to a whole neighborhood of collaborators; he cofounded the indie label Anticon and has collaborated with dozens of musicians, rappers and remixers.

The version of Why? that will play this week is a four-piece that can handle the more pop sound of his latest songs. And Wolf notes that the process is a little different now that he’s playing for a bigger audience. “I’d say things are a little more formulized — like, the things that I used to call finished recordings are now my demos. Maybe I’ll want to have a real guitar player doing this part, or have some horns do what I’d been doing on synth. Other than that, I try not to let it affect my songwriting. You want to write like you’re still in the bedroom, just to keep things honest.”