Clay Jackson, also known as "The Pain Giver" or even "PG", is a famous gangster rapper in the GTA IV era.
In 2008, he has one or more commercially successful albums to speak of, and is releasing his next entitled Love Isn't A Crime. He has unsuccessfully tried his hand at acting (one paparazzi shouts at him during the Hercules incident "how does it feel to be the worst actor in America, Clay?"). Rumors of his homosexuality also surfaced, and he had been spotted before with his blonde male boyfriend Jacob (as seen on The Celebinator's blog).
He is seen in person during the Club Management side missions, in which Luis is tasked with going to Hercules, rescuing Clay and his boyfriend Jacob (hiding from paparazzi inside his tinted PMP 600), and driving them back to the Majestic Hotel. He screams out excuses to the paparazzi, saying he was only at the bar to watch sports and/or audition male dancers for a music video, and that he is very homophobic. Once he has privacy, he is much calmer and more social with Luis, explaining that he and Jacob are also business partners, he is planning to buy Jacob expensive sneakers from Japan (a reference to BAPE, an extremely high-end urban clothing line from Japan) and even offers to invite Luis into the hotel suite, saying he looks lonely.
Jackson is likely based on a collection of New York gangster rappers such as Big Punisher (due to his nickname Pain Giver), Ja Rule and most prominently 50 Cent due to the similarity of his name (C. Jackson), his foray into acting and the fact that he started off making "hood" music before moving on to a more RnB oriented sound (as hinted at by the title of his new album). His closeted sexuality is inspired by the book Hiding in Hip-Hop by Terrance Dean, which suggests that many prominent black male actors, singers and rappers were secretly gay. His alias "P.G." (also short for Parental Guidence) is likely a double etendre relating to the pop oriented nature of his songs.
Jackson is voiced by Brooklyn rapper Poison Pen.