On January 5, 2016, MSNBC Hardball host Chris Matthews interviewed Hillary Clinton in an Iowa fire station during the Democratic primary season. Network footage obtained by the Cut shows Matthews, during the interview setup, making a couple of “jokes” about Clinton. He asks, “Can I have some of the queen’s waters? Precious waters?” And then, as he waits for the water, he adds, “Where’s that Bill Cosby pill I brought with me?” Matthews then laughs, delighted with the line, for an extended moment, as the staffers around him react with disbelief, clearly uncomfortable. (Cosby has been accused of sexual impropriety by dozens of women, some of whom allege that they were drugged and raped by the comedian.)

“This was a terrible comment I made in poor taste during the height of the Bill Cosby headlines,” Matthews said to the Cut. “I realize that’s no excuse. I deeply regret it and I’m sorry.”

Matthews has a long history of talking disparagingly about Hillary Clinton, whom he once called “witchy,”and often seems to channel what a hypothetical sexist Republican might say about a woman candidate: “she-devil,” “Madame Defarge.” In 2005, he wondered whether the troops would “take the orders” from a (female) President Clinton. “Is she hemmed in by the fact that she’s a woman and can’t admit a mistake,” he asked in 2006, “or else the Republicans will say, ‘Oh, that’s a woman’s prerogative to change her mind,’ or ‘another fickle woman’? Is her gender a problem in her ability to change her mind?” He once pinched her cheek following an interview, and, though he later apologized, on another occasion suggested that she only got as far as she did on the political stage because her husband had “messed around.”

In the 2016 interview that followed the Cosby reference, Matthews — whose wife, Kathleen, ran for Congress that same year, and faced what her campaign suggested were unfair questions about whether her husband’s career had helped her own — interrogates Clinton about the GOP’s fixation on her stamina, and brings up her husband’s infidelity. “Half my viewers are women. And they want to hear what it takes for a woman to just rise out of a situation which is pretty bad and come out of it and say, You know what? I can rise to this occasion. How did you do it?” he asks, before interrupting several times as she tries to answer.

Matthews also lingers on the question of whether it’s important “culturally” for women to be in military combat roles (“swinging on ropes into whatever valley you got to go kill people in”). “ I am a huge supporter of women being able to break whatever glass ceilings are holding them back …” Clinton answers, before Matthews cuts in to add: “If they can physically handle it.”

In December, the Daily Caller reported that Matthews was officially reprimanded for sexual harassment two decades ago; the producer who brought the complaint reportedly received separation-related compensation.