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Steers was born in Washington, D.C. His father, Newton Ivan Steers, Jr. (1917–1993), was a Republican congressman from Maryland. His mother, Nina Gore Auchincloss (born 1937), was the daughter of stockbroker and lawyer Hugh D. Auchincloss, a cousin of Louis Auchincloss, as well as a stepsister of Jacqueline Kennedy Onassis and the younger half-sister of the writer Gore Vidal. Steers is a relative of vice president Aaron Burr, the third Vice President of the United States. Steers' great-grandfather, Thomas Gore, served as Oklahoma's first Democratic senator, from 1907 until 1921 and from 1931 until 1937, while his great-great-grandfather, Oliver Burr Jennings, was a founder of Standard Oil. Steers' godfather is former Virginia Senator John Warner.

His brother Hugh Auchincloss Steers (1963–1995) was an American figurative painter whose later works often focused on AIDS as a theme. He has another brother, Ivan Steers, and five stepsiblings from his mother's second marriage to editor Michael Whitney Straight.

Steers grew up living in Bethesda, Maryland and Georgetown, Washington, D.C., where he attended St. Albans School. Steers was expelled from both the Hotchkiss School and Culver Military Academy. He eventually earned his GED and attended New York University.

Steers has had minor roles in a few of Quentin Tarantino's films, playing Roger (or "Flock of seagulls") in Pulp Fiction and providing one of the radio voices in Reservoir Dogs. He also has appeared in The Last Days of Disco, Fix and Gore Vidal's Billy the Kid.

He wrote and directed Igby Goes Down in 2002, an acidic, urban, coming-of-age film that starred Kieran Culkin and Susan Sarandon. Steers also was the screenwriter of the film How to Lose a Guy in 10 Days, which starred Kate Hudson and Matthew McConaughey. He has directed episodes of the television series Weeds, The L Word, Big Love, and The New Normal. Steers also directed the 2009 teen comedy film, 17 Again starring Zac Efron.

In 2010 Steers directed the drama Charlie St. Cloud, also starring Efron. Also in 2010, there was media coverage for Steers' being hired to direct an epic film about the early life of Julius Caesar to be based on the novels by Conn Iggulden as adapted from the first two novels of Iggulden's series, The Gates of Rome and The Death of Kings, and covering the years from 92 BC to 71 BC. Exclusive Media Group hired Steers after having the adaptation written by William Broyles and Stephen Harrigan. Steers directed the 2016 film adaptation of the parody novel, Pride and Prejudice and Zombies.