James Charles
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40 free James Charles trivia questions with answers — pop culture quiz, new questions added Oct 2026.
James Charles was a high-school student in upstate New York when a single tweet turned him into one of the most recognisable faces in online beauty. Within weeks he had a national advertising contract that no boy had held before him, and within three years he had an eight-figure following, a sell-out product range and the kind of fame that can stop traffic. This quiz follows the whole story. It covers his childhood and family, the first videos, the brand deals and product launches, the celebrity guests who have sat in his makeup chair, the public fallings-out that cost and won him followers, and his later moves into television and music. A few questions test the makeup itself, from his signature touches to the tricks he shares with fans. It is written for fans who have watched since the early days and for anyone who only knows the headlines. Every answer comes with a short explanation, so you will pick up the details you missed.
30 of 40 questions with answers and explanations. Play the quiz
Q 01At 17, James Charles became the first male ambassador for which American drugstore makeup brand?
CoverGirl
CoverGirl signed him in October 2016, and he said he was the first of its faces to do his own makeup from scratch for every shoot.
Q 02What family word does James Charles use for his fans, a name also printed on his 2018 clothing line?
Sisters
Sisters is how he addresses his followers, and his Sisters Apparel shop also sold a hoodie printed with the word Brothers instead.
Q 03Which beauty YouTuber, a former mentor, publicly ended her friendship with James Charles in a 2019 video?
Tati Westbrook
Tati Westbrook accused him of disloyalty after he advertised a rival vitamin brand, then took the video down and later said two other YouTubers had pushed her into making it.
Q 04Which Dance Moms alumna let James Charles swap her usual sparkle for soft glam in a 2020 makeover?
JoJo Siwa
JoJo Siwa normally did her own hair and makeup and gave him a single try, and she went without her trademark bow, glitter and rhinestones.
Q 05James Charles used liquid latex in 2020 to make which reality-TV figure look clawed by a cheetah?
Kylie Jenner
Kylie Jenner had just launched an animal-print makeup collection, which inspired the look, and it was her second turn in his Halloween chair.
Q 06Which English city was gridlocked for hours in 2019 when James Charles opened a cosmetics store there?
Birmingham
Birmingham ground to a halt as about 8,000 fans packed the Bullring shopping centre for a public appearance that lasted roughly 30 seconds.
Q 07James Charles posted a solo cover of which hit song in January 2021, saying he was nervous to share it?
Drivers License
Drivers License was Olivia Rodrigo's brand-new single at the time, and he had been sharing song covers online for years alongside the makeup.
Q 08Weeks after his 2016 ambassador announcement, James Charles appeared as a guest on which daytime talk show?
Ellen
Ellen had him on while he was still a 17-year-old high-school student, and DeGeneres had herself fronted adverts for the same makeup brand.
Q 09During a May 2019 feud, James Charles became the first YouTuber to lose how many subscribers within 24 hours?
1 million
1 million left in a single day, a YouTube first, and his following kept falling until a 41-minute reply video turned opinion his way.
Q 10James Charles's first YouTube channel, JaysCoding, covered the competitive modding scene of which video game?
Mario Kart Wii
Mario Kart Wii modding filled the channel he launched in 2010, along with song covers, five years before his first makeup video.
Q 11Which cosmetics company made the 39-shade eyeshadow palette James Charles released in November 2018?
Morphe
Morphe priced the palette at $39, a dollar a shade, and both it and his clothing line sold out within minutes of going on sale.
Q 12James Charles hosted, directed and co-produced which reality competition series that premiered in April 2020?
Instant Influencer
Instant Influencer put six up-and-coming makeup artists through challenges for a $50,000 prize, and it was filmed that January, before lockdowns began.
Q 13James Charles's first adverts as a brand ambassador in 2016 promoted So Lashy, which kind of makeup product?
Mascara
Q 21James Charles's 2019 advert for which vitamin brand upset a friend who co-owned a rival supplement company?
SugarBearHair
SugarBearHair competes with Halo Beauty, the vitamin line his friend had co-founded, and he said he posted the advert after the brand supplied him with security.
Q 22James Charles goes by his first and middle names; which surname, shared with an American poet, is his?
Dickinson
Dickinson is the family name of his parents, Skip and Christine, and his brother drops it as well, working as Ian Jeffrey.
Q 23In a 2018 Shane Dawson documentary episode, James Charles used makeup to turn Dawson into which beauty mogul?
Jeffree Star
Mascara was the product, and he was already on set filming his first television commercial for it when the appointment was announced.
Q 14Which pop singer and fellow brand ambassador announced James Charles's 2016 makeup deal on her Instagram?
Katy Perry
Katy Perry also surprised him on the commercial set, where the first clue she had arrived was her dogs running around the studio.
Q 15James Charles went viral in 2016 with a tweet saying he retook his senior photos with which item in tow?
A ring light
A ring light came along, he joked, so that his highlighter would show up on camera, and the post drew tens of thousands of likes and retweets.
Q 16James Charles's younger brother, Ian Jeffrey, left YouTube at 16 to pursue which career in New York City?
Modeling
Modeling took him to New York, where he signed with the IMG agency and walked runways, saying that being known online was not for him.
Q 17Which vlogger joined James Charles and the Dolan Twins for four rounds of same-day videos in 2018?
Emma Chamberlain
Emma Chamberlain had only just moved south from the Bay Area when the foursome formed, and the group earned a Shorty nomination for best YouTube ensemble.
Q 18Days before his May 2019 subscriber crash, James Charles walked the red carpet at which New York event?
The Met Gala
The Met Gala fell on May 6 that year, and by the following Monday his channel was shedding subscribers faster than any had before.
Q 19James Charles left upstate New York after high school for which city, where he bought a mansion in 2020?
Los Angeles
Los Angeles is where he moved into a five-bedroom house in September 2018, and by that December he was asking fans to stop turning up at his door.
Q 20Which 2019 summer venture did James Charles cancel the day after his 20th birthday, refunding every buyer?
A US tour
A US tour of two dozen cities was scrapped, though he insisted the decision was his own and that no venue or sponsor had pulled out.
Jeffree Star was the subject of the series, and the makeover episode let Dawson spend a day trying to live in his shoes.
Q 24James Charles names Nikkie de Jager and which American beauty YouTuber as his two biggest influences?
Jaclyn Hill
Jaclyn Hill, whose Champagne Pop highlighter sold 25,000 units in 20 minutes, remained a favourite of his even after he got to know her personally.
Q 25Which name did James Charles give the self-funded makeup brand he launched in 2023 after four years of work?
Painted
Painted opened with cream colours in ten shades, packaged in tubes like art supplies, and he said every dollar came from his own savings.
Q 26Which online-video honours named James Charles's 2020 makeup competition series their Show of the Year?
The Streamy Awards
The Streamy Awards honoured him three times in all, twice in the Beauty category and once for this series, which he also directed.
Q 27What does James Charles spritz onto his brush before dipping into highlighter, for an almost metallic glow?
Setting spray
Setting spray on the brush makes the shimmer pop, a trick he shared in his first interviews, joking that his glow ought to be visible from space.
Q 28Which singer, a friend James Charles met at Coachella, sat for his neon pink cut-crease look in 2020?
Doja Cat
Doja Cat told him that TikTok dance challenges had reshaped her whole career, and he crowned her the queen of TikTok songs.
Q 29Which pop singer filmed a makeup video with James Charles in 2019 to promote her own new beauty line?
Kesha
Kesha named every eyeshadow shade in the line after one of her songs, and he told her he had grown up listening to her music.
Q 30James Charles did which rapper's makeup for her 2019 single Sally Walker, then appeared in its video?
Iggy Azalea
Iggy Azalea set the video at a funeral, and he makes a cameo in it, as do three RuPaul's Drag Race queens.