The comparisons of Lindsay Lohan to Marilyn Monroe continued at Saturday night’s Two by Two for AIDS and Art gala when artist Richard Phillips’ latest portrait of Lohan brought in the night’s record bid of $300,000. More than $4.5 million worth of art sold at the event with proceeds being split between the Dallas Museum of Art and the American Foundation for AIDS Research.

Reminiscent of Warhol’s Marilyn portraits, Lindsay V was the second Phillips painting of the actress to bring a big number at the Dallas gala.

In 2010, another Lohan painting sold in Dallas for $360,000. “A mutual friend shared a picture of that work with Lindsay,” Phillips says. Soon, the artist and the actress were in touch. “We began texting each other.” She agreed to do a 90-second film for Phillips to be shown at the Venice Biennale. The painting sold Saturday night, was based on a still from the Venice movie. “It’s the iconic image from that film,” says Phillips.

Below, with an assist from Howard Rachofsky, Sotheby’s auctioneer Jamie Niven gavels down Lindsay V for $300,000 as Phillips watches from a table with Dallas Cowboys exec Charlotte Anderson.