You might have seen them on the pages of the New York Times and Interview. Or on the walls of MOMA, Tate Modern or the Modern Art Museum of Fort Worth. You may have even seen one on Gossip Girl.

If you’ve ever viewed a painting by Richard Phillips, you’d know it. Super-sized and hyper-realistic, his distinctive works lodge in the viewers’ minds long after they turn away from the wall. This weekend, the artist himself takes center stage at the annual Two x Two for AIDS and Art, where he will be honored with the amfAR Award of Excellence for Artistic Contributions to the Fight Against AIDS.

Phillips started his career in the early ’90s as a sculptor and line artist. He refined his iconic style of oil painting shortly before his first Dallas exhibit at Deep Ellum’s Turner & Runyon Gallery in 1997.

“It was a really ultra-important moment for me,” Phillips recalls. “John and Kenneth [Runyon and Turner] saw my show at [New York’s] Edward Thorp Gallery in 1996 and took that risk on me. I was completely unknown at the time, but many of those paintings I did for them are truly the most iconic paintings I’ve ever done. It was very prescient, and the support I got from the people of Dallas at the time has stayed with me throughout my career.”

In fact, Dallasites have swayed the artist’s focus, however inadvertently. A fortuitous studio visit by Two x Two co-host Howard Rachofsky led to Phillips’ donation of his Lindsay Lohan portrait Red, Blonde, and Blue — which sold in 2010 for $360,000 — as well as becoming the catalyst for all the work Phillips has created since.

“Dominic Sidhu, who became eventual creative director on my films, was on a shoot with Lindsay and showed her a picture on his cell phone of Red, Blonde, and Blue,” Phillips says. “She was quite surprised, so he suggested that we work together.”

The result was a collaboration between Phillips and legendary surf filmmaker Taylor Steele starring Lohan, which premiered at the 2011 Biennale di Venezia before going viral on YouTube, garnering millions of hits.

When certain stills of the film became placeholders on blogs and websites, it drove the singular images Phillips would choose for his next set of paintings. Moments from shorts he directed of Lohan and the actress Sasha Grey became paintings for his recent critically debated show at New York’s Gagosian Gallery, inverting the artist’s usual process. One of these — Lindsay V — will be auctioned off Saturday night at the Rachofsky House during Two x Two.

Although his recent work may seem a continual exploration of the meaning of celebrity, Phillips says it’s less about the famed and more about how “art aligns itself with different structures of influence.” His recent painting of Mitt Romney for the We The People exhibit at the Robert Rauschenberg Foundation is one of the largest in his career and no doubt his most multilayered.

“The value of how we look at it changes on a day-to-day basis,” he says. “When we first hung it, [Romney] was down in the polls, and the next day he won the debate. It’s not an ironic or satirical political painting used to denigrate a candidate; it’s a straightforward presentation of the political image, how it engenders trust and desire and competency. All of these things can only be brought forward if you leave aside the binary gesture of ‘this is bad’ or ‘this is good’ and see things as they are.”