(image via Plan B skateboards)

Paul Rodriguez, aka P-Rod, has kicked, pushed and flipped his way to two consecutive X-Games gold medals, a lucrative contract with Nike, and appearances in Tony Hawk’s Pro Skater video games – but don’t expect to see him doing stand-up anytime soon.

The 22-year-old California native, son of comedian and actor Paul Rodriguez, could have followed in his famous father’s footsteps, but became a pre-teen skateboarding prodigy instead, mixing natural talent with a knack for switch-stance tricks that belied his young age. Even during his days as an amateur with DNA and City Stars skateboards, Rodriguez was highly regarded for his effortless style. In 2002, after years of being called a “golden child,” Rodriguez turned pro with Girl skateboards. The Torrance, California based company added P-Rod to a talented stable of skaters that included Eric Koston, Rick Howard and Mike Carroll.

Two years later, Nike signed the youthful and charismatic P-Rod to a multi-year endorsement deal – rumored to be in the millions – prompting many purists to brand him a sellout. Rodriguez, however, says he was more concerned with securing his future – without the help of his father – than developing his street cred. “Growing up, I didn’t want to be 30 or 40 years old and realizing my whole career was made from someone else doing it for me.” Rodriguez was the first Nike team member to receive a signature shoe, the Paul Rodriguez Air Zoom. Over 20 colorways of the shoe have been released.

In recent years, P-Rod has moved to Plan B skateboards, collected a second X-Games gold medal, and taken up acting. He appears in two movies scheduled for release later this year. Perhaps the ultimate testament to his success as a skateboarder: you can now be P-Rod in Tony Hawk’s Project 8, his third appearance in the popular video game series.

Mr. Cartoon, aka Mark Machado, has tattooed Eminem, Beyoncé, 50 Cent, Dr. Dre, Justin Timberlake, Kanye West, Pharrell, Nas, Travis Barker and Xzibit – but tattooing is just a side gig.

A street kid through and through, the 37-year-old Mr. Cartoon began his career writing graffiti and drawing murals. At 16, he landed a job as an illustrator for Hustler magazine, eventually moving on to T-shirt designs and album covers for artists Cypress Hill, Maldita Vecindad and Transplants.

But it was a later foray into fine-line tattooing – a style that flourished in California prisons and has become synonymous with gang culture – which he credits with his current success: "[T]attoos reach everybody, because someone can somehow relate. If I walk into a nightclub, I can find only a handful of people that want an album cover, but can find at least 20 people who want tattoos."

Art directors eager to tap the authenticity of working class, Mexican-American street culture have taken notice. Mr. Cartoon was commissioned to design six shoes for Nike, including his personal choice, the Cortez. Vans produced three Mr. Cartoon-designed colorways of their Authentic shoe while T-Mobile put out a Mr. Cartoon edition Sidekick II. If you've played or seen commercials for Grand Theft Auto: San Andreas, you've seen more of his handiwork.

A savvy entrepreneur, the 37-year-old is also the co-owner of the Joker clothing brand and will soon release his own toy figure. In the quintessential nod to the American Dream, Brian Grazer, the producer of Apollo 13 and A Beautiful Mind, signed Mr. Cartoon to a three-picture deal, including a movie based on Machado's own life story which debuts in late 2007.