He Knows From Problems

You think you have problems?

Let Kaylib tell you about some of his.

He was driving around town with some friends …

… when a cop pulled him over for no good reason. Slammed him on the hood.

Then the judge … well, he wasn’t exactly sympathetic.

“Buy me a drink?” a woman asked Kaylib later on at the Taurus Cafe. Kaylib would have loved to have bought her a drink. But he had no money; that’s why he ​“pregamed” before showing up.

Then he came home to find a raccoon in his apartment. As though the critter lived there. A raccoon that seemed to be following him everywhere.

“That,” Kaylib declared, shrinking back to the door, ​“is a problem.” (Or, depending on which version of the song you hear, a ​“motherfucking problem.”)

True-Life Problems

Kaylib — a.k.a. 22-year-old Caleb Negron — tells those stories in a new song and video released this week. The song’s tight; the video’s a scream, in no small part thanks to Kaylib’s chops in front of the camera. An experienced musician and beat performer, he’s looking to launch a career.

In real life, Kaylib hasn’t encountered all the problems found in the song and video. But he knows from problems. He drew on how it felt to wrestle with some real problems to strike a universal note.

Because his road to launching a recording career hasn’t been a smooth one.

The teen years were tough. Especially when his family lost its home in a fire during his sophomore year in high school. His family was homeless for two weeks. He eventually crammed into an apartment atop a garage with relatives for the rest of high school.

Kaylib (he decided to spell it that way because of another problem — people couldn’t pronounce his name right) had some focus and direction. He had been performing in public since he began drumming for the 2nd Star of Jacob Pentecostal Church band at 8 years old. In junior high at Betsy Ross, he picked up some animation and video skills. At Cooperative Arts & Humanities High School, he learned how to produce beats. ​“I fell in love with that,” he said. He played drums, congas, sax, and piano in a jazz ensemble.

But Kaylib also got caught up ​“in some things I shouldn’t have gotten caught up in,” he said. He declined to identify those ​“things” — call it a ​“paper route,” he said. ​“Thank God” he never got locked up, he added.

Senior year he started applying himself. He earned honors for the first time. He finished high school determined to make a creative career for himself. He got some modeling gigs. He developed a party promotion side business. Meanwhile he had his eyes on a recording career.

That quest eventually led him to the door of Joe Ugly of Ugly Radio, the Chapel Street web radio station and studio where aspiring New Haven rappers have been known to come knocking.

“Do you rap?” Joe Ugly asked him.

Yes, Kaylib said.

“Get in the booth,” Ugly said.

Kaylib got in the booth. He rapped. About gunplay. About weed. About ​“chicks.”

Just as every other aspiring Fifty Cent does when he walks into Ugly Radio.

To Joe Ugly, that was a problem.

“When you’re ready to start rapping,” he told Kaylib when he emerged from the studio, ​“let me know.”

But Joe Ugly also saw promise. ​“He had that cadence,” Ugly said. ​“He know how to hold a beat. That’s how you can tell a true rapper. He was holding the beat, but he was rapping about nothing.”

Debt Crisis

Kaylib said he was up for rapping about something real. Joe Ugly agreed to work with him to produce tracks, and suggested that Kaylib research Puerto Rico’s debt crisis. (Kaylib’s family is Puerto Rican.) So Kaylib read up on the island’s economy, its bond woes, the effect on migration to the mainland.

Then he put together lyrics. Joe Ugly helped him refine them. They added a beat and put together a track called “Evil Man.”

They played it on Ugly Radio. But they decided against releasing it as a single. It didn’t feel quite like a hit.

They put together more tracks. They were solid, but they didn’t sound like hits, either.

Then a phrase popped up in Joe Ugly’s mind one Saturday when he was in the bathroom: “This is gonna be a problem.”

He called Kaylib. “Write this down,” he said. “What can you do with this?”

Kaylib worked up lyrics and together a beat. He and Ugly refined it into “Problem.” And, they decided, they had a potential hit. The track was danceable, ready for the clubs. It was fun. People could relate to it.

They linked up with a leading local rap performer and video producer Ale The Man. They brought along friends and members of the Ugly Radio crew to shoot the scenes in the car and at Taurus Cafe (where Ugly Radio’s DJ Rob Nice has a regular gig) and a Whitneyville church doubling as a courtroom (complete with DJ Rob Nice in the above-pictured judge’s robes).

Ale The Man used CGI effects to add the raccoon that causes problems throughout the video in between displaying some slinky dance moves (above) at Taurus.

Kaylib and Joe Ugly dropped the video on Tuesday, then started going to work trying to parlay it into a career-launching hit. (The video appears further up in this story.) They’re developing ​“Problem” merch and trying to secure opening acts for Kaylib for touring rap headliners.

Meanwhile, Kaylib is working two retail jobs (at Broadway’s Urban Outfitters and a Milford prom store) and taking courses in business administration and marketing at Gateway Community College. Waiting for that big break. Hoping ​“Problem” is the one.

“I feel ready,” Kaylib said. ​“I feel good. I’m excited.”

In other words, he’s got this. No problem.