Shortly after O'Reilly was ousted from Fox News, Watters took his own vacation from the network after coming under fire for making a comment about First Daughter Ivanka Trump, which some interpreted as inappropriate sexual innuendo.
Watters' recurring segment on "The O'Reilly Factor" involved sending the host out to various events and locations across the country for man-on-the-street style interviews that mock various cultural subgroups in their own communities. In a 2016 segment, Watters went after Italian Americans at the Feast of San Gennaro festival.
One of Watters' most controversial segments came in the form of a 2016 venture into New York's Chinatown. In the heavily criticized piece, Watters turned his signature schtick on Chinese Americans, resulting in a blatantly racist segment that played on Asian stereotypes and openly mocked its subjects.
Watters' October 2016 venture to the Amish community in Pennsylvania was turned into one recurring punchline -- over the fact that the Amish don't vote or pay much attention to presidential politics. "Lucky you," he tells several people.
In 2007, O'Reilly sent Watters to ambush Bill Moyers in the street after the PBS host released a documentary criticizing the Bush administration for the Iraq War. Bill O'Reilly would later go on to call that segment a contributing factor in Moyers' decision to retire.
In 2015, Watters went to Penn Station to criticize the "rise of homelessness" in New York City, pointedly asking those sleeping at the station about their drug habits and what they did to make money on the streets.
On the anniversary of 9/11, Watters went to a convention for Muslim Americans to ask them about terrorism and Islamic radicals. When a woman criticized the media for linking terrorism to the Islamic religion, Watters and O'Reilly both balked at the suggestion that "Christian terrorism" could even exist.
In 2009, Amanda Terkel, then the managing editor of Think Progress, wrote a column in which she said she was "followed, harassed, and ambushed" by Watters while on vacation after she ran a column criticizing Bill O'Reilly for his comments toward rape survivors.
Watters was caught on video getting into a fight at the 2016 White House Correspondents' Dinner afterparty with The Huffington Post's Ryan Grim. It was later reported that Grim approached Watters with a camera asking him to apologize to Terkel for his behavior in 2009.
O'Reilly sent Watters to Philadelphia for a tone-deaf segment about racism in which he mocked the Black Lives Matter movement, criticized political correctness and generally failed to elevate the conversation surrounding race relations in America.