It's Chess, Not Checkers, With West Palm Beach Rapper Rook

To some, the name Rook may indicate "rookie," but 22-year-old Anthony Joseph DeMaio took the name from the chess piece. Today, Rook is lucky if he's able to find time for the game he played regularly as a child, as taught to him by his grandfather. 

Originally from Bridgeport, Connecticut, Rook made the move to West Palm Beach to pursue a degree in cinematography and film at Palm Beach Atlantic College. It wasn't until his junior year of college when Rook started to take rap seriously. 

Before making his name in music, he helped pen clever punch lines and verses for his friends back home. The positive feedback fueled the rapper.

"It wasn't anything major, but that's when people started realizing, that's kind of hot," said Rook. "I kind of went with that and just started writing myself. It was kind of more like a nonchalant thing at the time, and then the more I started developing it, the more serious I started taking it."

The transition to hip-hop and rap happened later in life, having grown up listening to bands like Sublime, Adema, and Rage Against the Machine.

"As I was always around it, I just grew an ear for it, and I started looking into it myself and just kind of became a huge fan and got submerged in the whole culture," Rook revealed.

He purchased recording equipment to get a feel of how his raps sounded and chose to keep his activities to himself. His parents were not aware how serious he started to take his music until he brought it to their attention while closing a deal with MBassy Records.

"That was a struggle at first," Rook admitted. "Obviously, when I first gave them that call, that came out of left field for them. It took a little bit, but they're adjusted to it now, and they support me 100 percent."

Thanks to energy drinks and a lack of sleep, Rook was able to stick to the grind and juggle a part-time job, college, and his burgeoning rap career.

"Pretty much, I was going all day, and I would only get by on like four to five hours, maybe three to four hours some nights," Rook noted. "Pretty much full-time school all day and then getting in the studio after."

While promoting and throwing parties at small venues, the rapper built a network of friends and students in college, and through an off-hand comment made by a fellow promoter to people at MBassy, Rook's songs were given a listen to. Not too long after, MBassy approached Rook while he was working as a valet at Café Centro in West Palm Beach. The rapper signed with the label.

The same network Rook developed also helped him gain notoriety. Someone entered him as a nominee for the Palm Beach Music and Entertainment Awards in the Best New Artist category. Votes for Rook shot up to number one within a few hours and gained the attention of singer and songwriter Muzik Jones Drew, well-known in the West Palm Beach music scene.

"I automatically got attention from that, whether they liked me or not," said Rook, "and Muzik Jones Drew's people, who were the people from Kloud Clothing, they happened to see me, and they liked the music, so they hit me up for that cypher."

That cypher is the Jedstarz Cypher Pt. 2, which has more than 11,000 views on YouTube and includes fellow Palm Beach veteran rappers 1Hot, Vandam, J-20, and Makiin.

About a week later, Rook received a text from Drew asking him to feature on "Falsettos & Fly Sh*t." The two have since shot a video for the single and collaborated on other songs that will be released soon.

This past June, the rapper released his first mixtape, The Delorean Disc, with labelmate Iggy G. and his first solo mixtape, The Hometown Hero, in November.

"That was more of the EP to put anything out, since I hadn't put anything out in a while since Delorean," said Rook. "So I just wanted to give my close network of people some new music that I'd been working on so they could hear what I've been doing."

The mixtape is a collection of seven songs serving as an introduction, with radio-friendly singles like "Living Like I Should" and songs such as "Never Know" and "Go Baby" that give the listener a peephole-sized glimpse into the man behind the game.

Rook is set to release a new mixtape early this year called Collected and Connected that will feature 14 songs and reworked songs from The Hometown Hero.

Now, with more room on his plate after graduating college in December and no longer working as a valet, Rook is able to position his pieces to make bigger strides. If the past year is any indication of his work ethic, then listeners may have to stick around till somebody gets the queen.

Upcoming Events

Sponsor Content


All-access pass to the top stories, events and offers around town.

  • Top Stories


All-access pass to top stories, events and offers around town.

Sign Up >

No Thanks!

Remind Me Later >