Jake Paul
0Loading crowd target
0Loading crowd target
7correct to beat the crowd
50 free Jake Paul trivia questions with answers — pop culture quiz, new questions added Oct 2026.
Few internet stars have reinvented themselves as often as Jake Paul. He went from posting comedy clips as a teenager in Ohio to a role on a kids' sitcom, a run of singles that people loved to hate, and then a boxing career that put him in the ring with former world champions far older or far bigger than he is. This quiz follows the whole story: the early videos and the influencer house, the songs and the feuds, the knockouts, the losses and the famous opponents, plus the businesses, relationships and controversies that kept him in the headlines. It is written for fans who think they know everything about him and for curious boxing or YouTube watchers who only know the name. The questions run from easy openers to tough ones for the real experts, and every answer comes with a short explanation.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Which future Grammy-winning pop star co-starred on the Disney Channel sitcom Jake Paul left in 2017?
Olivia Rodrigo
Olivia Rodrigo played guitar-strumming Paige Olvera, half of the comedy-song duo at the centre of the show. Her debut single 'Drivers License' arrived less than five years after the premiere.
Q 02What did Mike Tyson give Jake Paul at their 2024 weigh-in after Paul stepped on his toe?
A slap in the face
A slap in the face was Tyson's instant reply. He said afterwards that he had been standing in socks while Paul wore shoes, and that the pain made him 'reciprocate'.
Q 03Which injury, needing two titanium plates, did Jake Paul suffer in his 2025 loss to Anthony Joshua?
A broken jaw
A broken jaw put Paul in hospital after Joshua floored him four times and stopped him in the sixth round. Surgeons also removed some teeth, and he could not eat solid food for at least a week.
Q 04Which former UFC champion got an 'I love Jake Paul' tattoo after losing to him in 2021?
Tyron Woodley
Tyron Woodley had the words inked on his middle finger as Paul's price for a rematch, which came that December. Paul knocked him out in the sixth round and won ESPN's Knockout of the Year award.
Q 05Which YouTuber held a 2019 Las Vegas wedding with Jake Paul that was never legally binding?
Tana Mongeau
Tana Mongeau and Paul never obtained a marriage licence, and their officiant was not licensed in Nevada either. The ceremony was sold on pay-per-view for $50 and filmed for her MTV show.
Q 06On which app did Jake Paul find fame from 2013, building 5.3 million followers with comedy clips?
Vine
Vine limited every clip to six seconds, and Paul's had drawn two billion views by the time Twitter closed the app. By then he had already launched his YouTube channel.
Q 07Which streaming service showed Jake Paul's 2024 Mike Tyson fight to 65 million concurrent viewers?
Netflix
Netflix struggled under the demand, with around 90,000 outage reports in the hour before the main event as streams buffered. It was the most-streamed sporting event ever at the time.
Q 08Jake Paul's first boxing match in 2018 was against Deji, the younger brother of which YouTuber?
KSI
KSI topped the same bill against Jake's brother Logan, in a fight scored a majority draw. Jake stopped Deji in the fifth round of the co-feature.
Q 09Which 2017 Jake Paul single, mocked for the lyric 'England is my city', still went platinum?
It's Everyday Bro
It's Everyday Bro became one of YouTube's most-disliked videos, yet it climbed to number 91 on the Billboard Hot 100. Paul said the song was written, filmed and edited within a single day.
Q 10Whose hat did Jake Paul snatch to spark a brawl at a 2021 press conference for his brother's fight?
Floyd Mayweather
Floyd Mayweather, a five-division world champion, was filmed shouting threats at Paul after the grab. A month later Logan lasted all eight rounds of their exhibition.
Q 11In which Ohio city was Jake Paul born, where he headlined at Rocket Mortgage FieldHouse in 2021?
Cleveland
Cleveland gave him a hometown crowd at the Cavaliers' arena, where two of the three judges scored the eight-round fight in his favour. His official purse for the night was $2 million.
Q 12On which Disney Channel sitcom did Jake Paul play a dare-taking video star until his 2017 exit?
Bizaardvark
Bizaardvark blends 'bizarre' and 'aardvark', the name of the video channel run by the show's two teenage leads. Disney announced Paul's departure midway through filming the second season.
Q 13Which former Love Island contestant handed Jake Paul his first professional defeat in 2023?
Tommy Fury
Q 21In which country did Jake Paul suffer his first professional defeat, at the Diriyah Arena in 2023?
Saudi Arabia
Saudi Arabia staged the card in the town of Diriyah, with a world title fight on the undercard. Paul bounced back that August with a ten-round points win over a former UFC star.
Q 22Which US presidential candidate did Jake Paul endorse in a YouTube video on Halloween 2024?
Donald Trump
Donald Trump got Paul's backing five days before the election, a year after Paul had supported Vivek Ramaswamy in the Republican race. Trump later said he would endorse Paul for any political bid.
Q 23In 2022 Jake Paul co-promoted the first women's boxing match to headline which New York arena?
Madison Square Garden
Tommy Fury won on two of the three scorecards despite being knocked down in the final round. He had pulled out of two earlier dates with Paul, once on medical grounds and once over travel trouble.
Q 14Jutta Leerdam, who announced her engagement to Jake Paul in 2025, won Olympic gold in which sport?
Speed skating
Speed skating made the Dutch sprinter an Olympic champion in 2026, when she won the 1000 metres in a Games-record time with Paul there cheering. The pair first got talking over Instagram.
Q 15Which influencer collective, launched by Jake Paul in 2016, featured on his biggest hit single?
Team 10
Team 10 doubled as a talent business, and a former member later said on camera that every prank in the group's videos was staged. Its social accounts fell silent in 2019.
Q 16Which boxing nickname of Jake Paul's appears in the title of a 2023 'Untold' documentary?
The Problem Child
The Problem Child had already been shortened to 'PRBLM CHILD' for a hype series before his 2021 fight with Ben Askren. In 2024 it became a downloadable pack in the boxing game Undisputed.
Q 17Jake Paul beat Mike Tyson in 2024 at AT&T Stadium, the home ground of which NFL franchise?
Dallas Cowboys
Dallas Cowboys have played at the Arlington stadium since it opened in 2009, and the fight there produced the biggest boxing gate in US history outside Las Vegas. Paul won a unanimous decision.
Q 18Which medical issue made Mike Tyson postpone his Jake Paul fight from July to November 2024?
An ulcer flare-up
An ulcer flare-up struck Tyson aboard a plane in May 2024, pushing the bout back four months. Paul filled the vacant July date by stopping bare-knuckle fighter Mike Perry in Tampa.
Q 19Which former NBA slam-dunk champion did Jake Paul knock out cold in the second round in 2020?
Nate Robinson
Nate Robinson, the league's first three-time dunk champion, went down three times and was left unconscious on the canvas. The fight supported Mike Tyson's exhibition with Roy Jones Jr.
Q 20Which federal agency searched Jake Paul's California mansion after a 2020 riot at an Arizona mall?
The FBI
The FBI served a federal search warrant two months after Paul was filmed inside a Scottsdale mall as it was being looted. He said he was only documenting, and no federal charges followed.
Madison Square Garden hosted Katie Taylor's title defence, billed 'For History' and co-promoted with Eddie Hearn's Matchroom. Sports Illustrated named it Fight of the Year.
Q 24Which fight boss, later mocked in a Jake Paul diss track, offered to bet $1 million against him?
Dana White
Dana White, the UFC president, said he would stake the money on Ben Askren. Paul offered to double the wager, Snoop Dogg put up $2 million on Paul, and Askren lost inside two minutes.
Q 25Which WWE champion was Logan Paul facing when Jake Paul ran in to help at Crown Jewel 2022?
Roman Reigns
Roman Reigns kept his Undisputed WWE Universal Championship even after Jake took out The Usos at ringside. Jake had walked to the ring to his own 2017 single.
Q 26On which Caribbean island did Jake Paul buy a mansion in 2023 and beat Ryan Bourland a year later?
Puerto Rico
Puerto Rico hosted the Bourland fight at its Coliseo in San Juan, where Paul won by first-round technical knockout. Bourland arrived with a professional record of 17 wins and 2 defeats.
Q 27Which YouTuber made the eight-part 2018 documentary series 'The Mind of Jake Paul'?
Shane Dawson
Shane Dawson brought in a licensed therapist to help him ask whether Paul was a sociopath, a framing that drew sharp criticism. The series still passed 175 million views.
Q 28Which ex-girlfriend was the main target of Jake Paul's 2017 diss track and hit back with RiceGum?
Alissa Violet
Alissa Violet said Paul had thrown her out of the house his crew shared, months before he released the song. Her reply a week later charted higher, reaching number 80 on the Billboard Hot 100.
Q 29In which Florida city did Jake Paul make his pro debut in 2020 and fight Anthony Joshua in 2025?
Miami
Miami saw Paul stop fellow YouTuber AnEsonGib in the first round of his debut, on a card topped by a world middleweight title fight. The Joshua bout was held at the Kaseya Center.
Q 30Which retailer launched Jake Paul's grooming brand in 2024, with every product priced under $10?
Walmart
Walmart stocked the range, called W, from its June 2024 launch. A month later the Wall Street Journal reported that investors including tennis star Naomi Osaka had put in over $14 million.