Prior to their chat at an Iowa fire station, Matthews was recorded joking about in a way that made light of both Clinton and sexual assault.
"Where's that Bill Cosby pill I brought with me?" he quips seconds later, prompting nervous laughter and stunned faces from those around him.
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.
"This was a awful comment I made in poor taste during the height of the Bill Cosby headlines", Matthews told the magazine in response. "I realize that's no excuse".
Dog Treks Nearly 40 Miles Searching For Owners Who Gave Her Up
The animal shelter said she made the rip a second time after she was brought back to Prague. The humane society's post drew quite a bit of media attention.
Matthews, who has hosted MSNBC's Hardball since 1997, has a history of making sexist remarks toward Clinton. "I deeply regret it and I'm sorry".
An MSNBC spokesman confirmed Saturday the company made a separation-related payment to one of Chris Matthews employees after the woman complained about sexual harassment. An MSNBC spokesperson contested that claim to the Caller, saying the company instead paid significantly less as part of a severance package. Based on people who were involved in matter, the network concluded that the comments were inappropriate and juvenile but were not meant to be taken as propositions. "Precious waters?" Matthews was seemingly referring to Clinton.
It's not even the first time Matthews has targeted Hillary Clinton, though this clip lacks the blunt sexism of questions like "Is her gender a problem in her ability to change her mind?" something he asked in 2006.