LOL

These photos of Pitbull before he was famous are almost too Miami to handle

By Connie Ogle

Updated October 13, 2021 1:55 PM

These days, when you think of Pitbull, you think of the man with the sunglasses, the hits and the suit you couldn’t afford even if you got that raise you think you deserve.

But it wasn’t always that way.

Now, Pitbull is so big we think of him as a Miami superhero. But there was a time when nobody outside Miami could translate the word “Dale!” Back before he hosted New Year’s Eve celebrations and cranked out all the songs on your workout playlist, Armando Christian Perez was just a Miami kid with big dreams and dubious fashion sense.

And we have the photos to prove it.

So take a walk back in time with us to see the evolution of Mr. 305.

Most Miami photo ever

01/30/03 -- Barbara P. Hernandez / For the Herald -- Miami: Up and coming rapper, Pitbull, at his favorite barber shop, a grafitti-walled Little Havana hub where he gets a 12-dollar fade cut. Althought he’s yet unsigned, his records are blowing up the radio charts. (2 of 2) Barbara P. Hernandez For the Herald

In January of 2003, the Man Who Would Be Worldwide posed for a photo shoot at a Little Havana barber shop. Half the guys in your Coral Park High class looked exactly like this.

We don’t know what’s up with the line down his face either

01/30/03 -- Barbara P. Hernandez / For the Herald -- Miami: Up and coming rapper, Pitbull, getting a haircut at his favorite barber shop, a grafitti-walled Little Havana hub whre you can get a 12-dollar fade cut. His barber, 20-year old Josue Romero, is the son of the owner, and they have known each other for some years. (1 of 2) Barbara P. Hernandez For the Herald

We do know he used to pay $12 for a fade from barber Josue Romero, son of the shop’s owner.

305 4 Lyf

Vintage Pitbull is always fun. MARICE COHN BAND MIAMI HERALD STAFF

Looking good, Pit! Here he is in 2003 repping the 305 hard in the neighborhood he grew up in. (His mom’s house was at 25 NE 28th St.)

Sensitive Pit

02/04/03--MARICE COHN BAND/MIAMI HERALD STAFF--MIAMI; Pitbull, a rapper, hangs in the neighborhood he grew up in. His mother’s house, 25 N.E. 28th Street, a forgotten Miami area. Behind him on the tracks is Cubo. SOUTH FLORIDA (2 of 2) MARICE COHN BAND MIAMI HERALD STAFF

He is probably coming up with great lyrics like “This biggity boy’s a diggity dog.”

All that’s missing is a grill

TO DADE--05/28/04--RAUL RUBIERA Miami Beach -- Florida Following rapper Pitbull Rapper Vido (CQ) (left), producer Jim Jonsin (CQ) (center) and rapper Pitbull (CQ) react to the tv cameras in the streets of Miami Beach. Raul Rubiera

Pitbull had still not discovered suits in 2004, but he was all about that sideways baseball cap life.

No, seriously, this guy is going to look good in a suit one day

TO DADE--05/28/04--RAUL RUBIERA Miami Beach -- Florida DJ Select (CQ) hanging with rapper Pitbull Raul Rubiera

Even more sideways with DJ Select.

Pit and the Miami fans

TO DADE--05/28/04--RAUL RUBIERA Miami Beach -- Florida Rapper Pitbull and fans. Ariel Barak (CQ) and Brooke Silver (CQ) talk to rapper Pitbull at Club Deep in Miami Beach. Raul Rubiera

Pitbull meets fans at Club Deep in Miami Beach. Yes. Club Deep. You’re old.

The music

Miami, FL--11/23/04--Joshua Prezant/ for the Herald--Rapper Pitbull ( right) performs Tuesday night at the second annual Miami Awards at Players night club. Pitbull won several awards. Joshua Prezant/ For the Herald ©Joshua Prezant 2004

He performed at the second annual Miami Awards at Players night club in 2004. Still no suit.

We’re sorry about this one

Raw | Regional | YYYYMMDD | YYYYMMDDHHMMSS | YYYYMMDDHHMMSS+U00 — Raul Rubiera

He probably wants this shot from 2004 to disappear from the face of the earth. God knows we would.

This guayabera is everything

We fully believe Pitbull got this guayabera painted at the youth fair. manny hernandez for the Herald

Pit apparently took his guayabera to a Youth Fair booth and had someone spray paint it before posing at Calle Ocho 2005. We are pretty sure there’s a matching cap in his closet.

And tonight, let’s enjoy life

TO DADE--05/28/04--RAUL RUBIERA Miami Beach -- Florida Trick Daddy (on the left) parties with rapper Pitbull at Club Deep. Raul Rubiera

Here’s the thing about Pitbull: He always looks like he’s having a good time (here with Miami legend Trick Daddy). Probably because he always knew one day he’d be…

Mr. Worldwide

And he’d be doing stuff like this.

This story was originally published May 15, 2018 at 6:05 AM.