Wynn was born on October 21, 1988, in Arlington, Virginia, and raised in the same state. Wynn’s parents are a psychology professor and a doctor. 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. Wynn left Northwestern, saying it had become “boring to the point of existential despair”, and moved to Baltimore, Maryland, where she now lives.

Wynn started publishing YouTube videos in 2008, initially regarding religion and atheism. 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. Early ContraPoints videos also covered subjects such as race, racism, and online radicalisation. In her videos, Wynn uses philosophy, sociology, and personal experience to explain left-wing ideas and to criticize common conservative, classical liberal, alt-right and fascist talking points.

Wynn is a trans woman, a matter that features heavily in her videos, and began her gender transition in 2017. Wynn previously identified as genderqueer. She is a feminist and a socialist. As of 2017, she resides in Baltimore, Maryland. In 2020, Wynn came out as a lesbian in her video “Shame”.

In November 2018, after a ContraPoints video about incels reached over one million views, The New Yorker released a profile of the channel, describing Wynn as “one of the few Internet demi-celebrities who is as clever as she thinks she is, and one of the few leftists anywhere who can be nuanced without being boring.” The Atlantic praised Wynn’s use of “lush sets, moody lighting, and original music by the composer Zoë Blade” and opined of her videos that “The most spectacular attraction […] is Wynn herself.” Polygon named her video on incels one of the ten best video essays of the year 2018. In May 2019, she topped the Dazed 100 list, which ranks people who “dared to give culture a shot in the arm.”

Wynn’s videos often have a combative but humorous tone, containing dark and surreal humor, sarcasm and sexual themes. Wynn often illustrates concepts by playing different characters who engage in debate. The videos have been noted for showcasing Wynn’s production choices such as complicated lighting, elaborate costumes, and aesthetics. She takes aesthetic cues from drag performance, saying in a 2019 interview that if conservatives were going to call her a drag queen anyway, she decided to “be the most extravagant drag queen on YouTube.” In a 2018 interview for The Verge, Katherine Cross notes a significant difference between Wynn and how she presents on YouTube, explaining that the YouTube channel portrays an image of being “blithe, aloof, decadent and disdainful”, while personally Wynn “can be earnest—and she cares deeply, almost too much.”

In September 2019, Wynn described on Twitter feelings of awkwardness when asked in some contexts to describe her preferred gender pronouns. The tweets were criticized as dismissive of non-binary people who use pronouns other than “he/him” and “she/her”. Contrastingly, professor Lal Zimman opined about pronoun introductions, “Wynn is absolutely right that people engage with that practice in ways that can be somewhat problematic”. Following negative reaction, Wynn deactivated her Twitter account for a week, then posted an apology.

In October 2019, Wynn’s video “Opulence” featured a quote from John Waters read by transsexual pornographic actor Buck Angel, whose views on transgender people have attracted criticism, including by some who see Angel’s views as being transmedicalist. Wynn was criticised for featuring Angel, including by journalist Ana Valens. In addition to criticism, Wynn and YouTubers associated with her were widely harassed. Wynn’s January 2020 video “Canceling” addressed both criticism and harassment of her, and the broader context of perceived “cancel culture”. It was praised by Robby Soave of Reason.

In February 2020, Wynn set all her videos from before August 2017—when she began her gender transition—to private saying that they “no longer represent the person I’ve become”. She posted transcripts of the majority of these videos on her website.