Robinson of Current Affairs calls ContraPoints a "one-woman blitzkrieg against the YouTube right," describing her videos as "unlike anything I've ever seen. Regardless of the viewer's interest or lack thereof in internet culture wars, YouTube Nazis, or any of the other wide-ranging subjects covered in its videos, they're funny, bizarre, erudite, and compelling." Nathan J. In an article contrasting her personal sincerity and her ironic sense of humor, The Verge describes her as the " Oscar Wilde of YouTube." New York magazine states, "ContraPoints is very good.
Jake Hall, writing for Vice, called Wynn "one of the most incisive and compelling video essayists on YouTube". Wynn's videos have been praised for their clarity, nuance, and attention-grabbing sense of humor. As of May 2022, Wynn had about 11,000 Patreon supporters. The video channel is financed through the crowdfunding platform Patreon, where Wynn has been among the top 20 creators on the site. She borrows some aesthetic cues from drag performance, joking in a 2019 interview that if conservatives were going to call her a drag queen anyway, she might as well "be the most extravagant drag queen on YouTube." In a 2018 interview for The Verge, Katherine Cross notes a significant difference between Wynn in-person and how she presents on YouTube, explaining that the YouTube channel portrays an image of being "blithe, aloof, decadent and disdainful", whereas personally Wynn "can be earnest-and she cares deeply, almost too much." The videos have been noted for her production choices such as dramatic lighting, elaborate costumes, and vibrant aesthetics. She often illustrates concepts by playing different characters who debate one another. Wynn's videos often have a combative but humorous tone, containing dark and surreal humor, sarcasm, and sexual themes. In her videos, Wynn utilizes philosophy and personal anecdotes to not only explain left-wing ideas, but to also criticize common conservative, classical liberal, alt-right, and fascist talking points. Wynn uses costumes and colourful sets in her videos Early ContraPoints videos also covered subjects such as race, racism, and online radicalization. In 2016, she began the ContraPoints channel in reaction to the Gamergate controversy and the increasing prevalence of right-wing YouTubers, shifting her content to countering their arguments.
Wynn started publishing YouTube videos in 2008, initially focusing on criticism of religion and her position as an atheist and skeptic.
After quitting her PhD program, Wynn taught piano, and worked as a paralegal, Uber driver, copywriter and would-be novelist, eventually deciding to begin making video responses to the alt-right and Gamergate on YouTube. She left Northwestern with a master's degree, saying "The idea of being an academic for the rest of my life became boring to the point of existential despair," and moved to Baltimore, Maryland for a relationship, which ended up failing. After studying piano at Berklee College of Music, she attended Georgetown University in Washington, D.C., and studied philosophy, then enrolled at Northwestern University in Illinois to pursue a PhD in philosophy, also serving as an instructor. Her father is a psychology professor and her mother is a doctor. Wynn was born on October 21, 1988, in Arlington, Virginia, and raised in the same state.