The footage kicks off with Matthews asking: "Can I have some of the queen's waters?" Mr. Matthews made the offending comment as he was prepping for an interview with Mrs. Clinton at an Iowa fire station during the Democratic primary season on January 5, 2016, The Cut reported.
During the interview that followed, Matthews asked Clinton about her husband's infidelity and asked her whether it was "culturally" important for women to be allowed into military combat roles. While he's waiting for the water, he quips, "Where's that Bill Cosby pill I brought with me?".
Matthews said that it was a bad comment he made in poor taste when the Cosby case was in the headlines. "I deeply regret it and I'm sorry".
The release of the footage comes as the nation reckons with sexual assault and harassment, with near-daily revelations about men falling from positions of power in entertainment, business, the media and politics.
Matthews has always been known to have a combative relationship with former candidate Clinton. He once pinched her cheek after an interview, and, in 2008 said, "the reason she's a USA senator, the reason she's a candidate for president, the reason she may be a front-runner is her husband messed around". A rep from the network disputed that figure claiming the former employee was paid much less as part of a severance agreement, but didn't specify the amount.
Last month, Matthews, who has hosted his nightly talk show on MSNBC since 1997, was accused of sexually harassing a staffer at the news channel in 1999.
MSNBC confirmed the settlement to the publication and said Matthews received a former reprimand.
He also said, in 2015 upon hearing a rumor that she might quit the race, "when Hillary Clinton quits this election, we'll shut down the show".