Bolender began his career with a small role in the 1986 television film Dallas: The Early Years. He has been a part of several TV movies since. He has also made guest appearances in shows such as Star Trek: Deep Space Nine, Walker, Texas Ranger, NYPD Blue, The Alias, The West Wing, and others. He starred in five episodes of JAG between 1995 and 1998 as Captain Skipper Ross. Since his appearances on Avatar: The Last Airbender, he has appeared in episodes of ER and Cold Case.