After graduating from UNC, Holloman moved to Chicago to work with the Piven Theatre Workshop. She studied with John Lynn in Los Angeles, and was cast in David Orr's independent feature Blossom Time. She moved to New York City in early 1994 and appeared in stage productions such as Tennessee Williams' The Glass Menagerie, Carson McCullers' The Heart Is a Lonely Hunter at the Theatre for the New City. Holloman also performed off-Broadway in Julia Jordan's Night Swim at Playwright's Horizons. In 1995, Holloman began her film career with her role as Randy Dean in The Incredibly True Adventure of Two Girls in Love. She worked steadily in a variety of mostly independent film roles, such as The Myth of Fingerprints, Boogie Nights and Tumbleweeds. In 2005, Holloman appeared in Showtime's show The L Word as Tina Kennard. For this role, she was presented with a Golden Satellite Award in 2005 as Best Actress in a Drama series. Though she retired from acting to pursue a career in painting, she briefly returned to reprise the role in two episodes of the series' follow-up, .
Painting
After her acting career, Holloman spent her time in painting in Los Angeles. Her paintings were influenced by Mark Rothko, with vibrant use of color and large scale pieces, as well as elements of three dimensional effect. Although mostly abstract, Holloman's paintings betray a distinctly literary spirituality. She received favorable reviews for Free Falling, which was held at the Ateneo Veneto in Venice, Italy. Art critic Lea Mattarella reviewed Holloman's works in La Repubblica: "Holloman's paintings take us elsewhere, and at the end of the day, this is what art is all about". Holloman's painting, "Swell", was chosen to be part of the group show entitled "Nell' Acqua Capisco" at the Venice Biennale, 2013. She won 1st Place in Discipline Painting at the 2014 Contemporary Art Biennale of Argentina. Holloman had two entries in the 2015 Florence Biennale and won a prize for "Into the Woods". In November 2015 she had a solo show at the Menier Gallery in London titled "The Innocents". Holloman's first solo museum show entitled "Everglow" was held in Amstelveen, Netherlands from July 2016 through August 2016 in the Museum Jan Van der Togt.
Holloman married architect Paul Macherey on July 13, 2002. They have a daughter, Lola Reiko Macherey, who was born on November 4, 2004. They adopted a second daughter, Nala Belle on March 25, 2008. In 2011, Holloman filed for divorce, which was finalized on June 18, 2012.
