Berry holds degrees from Dartmouth College and Yale Law School. After graduating from college, Berry clerked for Clarence Thomas at the United States Supreme Court. After serving in the judicial branch, he joined the United States Department of Justice, where he helped to gain reauthorization of the USA PATRIOT act, and crafted legislation to follow the recommendations of the 9/11 commission. During his time at the Justice Department, Berry won the John Marshall award; the department's highest award for legal performance by attorneys.
Following his tenure at the Department of Justice, Berry served as Deputy General Counsel and then General Counsel for the Federal Communications Commission (FCC). As the Commission's highest legal officer, Berry was responsible for providing legal advice, as well as defending the Commission's orders in court.
Berry, who had never run for political office before 2010, raised more campaign funds then any other Republican candidate to run in the 8th district in recent years, with US$124,000 as of May 26, 2010. The Congressional seat that Berry ran for lies directly south of Washington, D.C. and includes all of Arlington County, the city of Alexandria, Virginia and part of Fairfax County. The district has been won by Democratic candidates in the past three presidential elections by margins often exceeding ten points, and Jim Moran, the former mayor of Alexandria, has held the district for nearly twenty years.
Berry is pro-life, and supported overturning the United States Supreme Court decision in Roe vs. Wade. He also claimed on his website to believe that "All Americans should be seen as equal under the eyes of the law". He also supports Second Amendment rights. Berry said that he wanted to end Congressional earmarking as well as to eliminate the Troubled Asset Relief Program (TARP). Berry's support of same-sex marriage and of repealing the military's Don't Ask, Don't Tell policy drew some criticism from conservative bloggers in Virginia.
In closing remarks at a debate with Patrick Murray at T.C. Williams High School in Alexandria, Berry said his campaign was better organized to run against Moran and could attract crossover Democrats and independent voters. "I don’t want us to be in a situation again where we’re bringing a knife to a gunfight," he said.
Berry was defeated by Murray narrowly on June 8, 2010. Prior to his defeat Berry had been the subject of mailers and calls sent out by the Murray campaign attacking his stance on gay rights issues.
Berry, who is openly gay, lives in Arlington, Virginia with his partner.