Penn Holderness is an actor, singer and entrepreneur. He was a former news anchor, sports director, reporter for ESPN, and host for HGTV. In 2013, he and his family first found fame when they released "XMAS Jammies" - a parody of Will Smith's "Miami" meant to be their family's digital Christmas card. Overnight, their video went viral on YouTube, garnering 15 million views in one week. They have been making videos ever since, known as The Holderness Family.

He and his wife, Kim, own their own company, Holderness Family Productions, where Kim is Chief Executive Officer and Penn is Chief Creative Officer. As well as creating content for their channels, they also work alongside brands and agencies to shape product launches and marketing campaigns. Their book about improving communication in a marriage was released in Spring 2021.

On broadcast television, the Holderness Family have appeared on The Today Show, Fox & Friends, Good Morning America, CNN, HLN, CBS This Morning, and multiple times on Right This Minute. Their full-length specials include The Holderness Family on UPTV, The 12 Foods of Christmas on The Food Network, and The Greatest Holiday Video Countdown on The CW.

He and his wife competed in season 33 of The Amazing Race.

He has appeared in the films Iron Man 3 (2013) as a news reporter, and Tammy (2014) as a news anchor.