Tolbert was a former college basketball star with the University of Arizona in the late 1980s. He played for various teams in the NBA including the Golden State Warriors, Charlotte Hornets, Orlando Magic and Los Angeles Clippers before retiring in the mid 1990s. With the Warriors, under coach Don Nelson, Tolbert was one of only a few players to play the point center (as opposed to the point guard) position.
In 1996, he joined sports radio station KNBR in San Francisco, California as an irreverent sports talk personality - teaming with Ralph Barbieri to form the highly rated afternoon show, The Razor & Mr. T. In addition to his radio work in San Francisco, he was a color analyst for NBA telecasts on NBC before moving on to ESPN. He was nominated for an Emmy in 2002 for his analyst work on NBC. In 2003, Tolbert along with Brad Nessler and Bill Walton called the NBA Finals for ABC.