Charles began his career in broadcasting in St. Louis, Missouri, as an overnight reporter, news writer and assignment editor at KSDK-TV. A year later, he became a weekend sports anchor at WDTN in Dayton, Ohio. After three years in Dayton, Charles became the weekend sports anchor at WHDH-TV in Boston.
From 2002 to 2006, Charles was the host of the weekly golf show, PGA Tour Sunday on USA Network, serving as lead anchor for studio segments during PGA Tour events.
Charles was also an anchor and reporter for NBC Sports, where he anchored the weekend Sportsdesk show and provided live reports and interviews for NBA on NBC. He also anchored sports at WNBC in New York City while working for NBC Sports.
Charles was portrayed in EA Sports' Madden NFL 10 as the main host of “The Extra Point”, a weekly recap show that broke down the highs and lows in a network-style show. Alex Flanagan was his co-host.
Charles made his MLB Network debut as studio host during the 2013 World Baseball Classic on March 9.[1] On February 20, 2023, it was reported that Charles had been let go by MLB Network.[2]