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48 free Two and a Half Men trivia questions with answers — entertainment quiz, new questions added Aug 2026.
49 free Two and a Half Men trivia questions with answers. Two and a Half Men ran for 262 episodes across 12 seasons, and this quiz covers both halves of it: the Charlie Sheen years of jingles, bowling shirts and Berta's put-downs, and the Ashton Kutcher years of Walden Schmidt, fake marriages and a long-lost daughter. Fifty questions on the cast, the characters, the guest stars and the off-screen drama that changed the show. It opens with easy ones (what does Alan do for a living?) and works up to production trivia and finale details only committed fans will know: the 100th episode's title, who was arrested as the Charlie lookalike, and how many Emmy nominations the show collected. Good for a solo run or a sitcom round at trivia night. Every answer has been checked against the show's Wikipedia entries and the pages on its cast and finale, and each question shows its source once you have answered.
30 of 48 questions with answers and explanations. Play the quiz
Q 01Which network aired Two and a Half Men for its entire 12-season run?
CBS
It ran from September 22, 2003 to February 19, 2015, and was later credited with making The Big Bang Theory, Mike & Molly and Mom possible.
Q 02What does Charlie Harper do for a living?
Jingle writer
He later performs children's music under the name Charlie Waffles.
Q 03What is Alan Harper's profession?
Chiropractor
His low earnings leave him paying alimony to two women and sponging off whoever owns the beach house.
Q 04In which California community is Charlie's beach house?
Malibu
Alan moves in after his wife Judith decides to divorce him, with Jake staying at weekends.
Q 05Who plays the sardonic housekeeper Berta?
Conchata Ferrell
The part was written as a two-episode arc; she ended up in every episode of season 11 and earned two Emmy nominations for it.
Q 06How is Rose, played by Melanie Lynskey, introduced in the pilot?
As Charlie's stalker
She was one of Charlie's one-night stands, and she is still stalking the household by the finale.
Q 07Who plays Charlie and Alan's vain mother Evelyn?
Holland Taylor
A high-powered Los Angeles realtor, Evelyn is five-times widowed; Taylor earned four Emmy nominations for the role.
Q 08Which actor played Alan's ex-wife Judith?
Marin Hinkle
Judith later marries Jake's pediatrician Herb Melnick, to Alan's delight, because it ends his alimony.
Q 09Which cast member is the only one to appear in all 262 episodes?
Jon Cryer
Cryer had auditioned for Gaius Baltar on Battlestar Galactica around the same time he was cast as Alan.
Q 10How many Primetime Emmy Awards did Jon Cryer win for playing Alan Harper?
Two
He won Outstanding Supporting Actor in 2009 and Outstanding Lead Actor in 2012, the year the show took three Emmys.
Q 11Charlie Sheen was fired in March 2011 after publicly attacking which producer in radio and TMZ interviews?
Chuck Lorre
CBS and Warner Bros. cited 'moral turpitude'; Sheen then sued for $100 million.
Q 12How much per episode was Sheen paid under the 2010 contract that made him TV's highest-paid actor?
$1.78 million
He had reportedly walked away from a $1 million offer as too low.
Q 13Which British actor was approached to replace Sheen before Ashton Kutcher was hired?
Hugh Grant
Kutcher's first line on hearing the news: 'I can't replace Charlie Sheen, but I'm going to work my ass off to entertain the hell out of people!'
Q 21How are the show's episode titles chosen?
A fragment of its own dialogue
They usually give no clue to what the episode is about.
Q 22Which CBS drama took part in a 2008 crossover with the show?
CSI
George Eads cameoed in 'Fish in a Drawer'; the CSI half, 'Two and a Half Deaths', was written by Lorre and Aronsohn.
Q 23Which of the show's 12 runs was cut to 19 episodes by the 2007-08 Writers Guild strike?
The fifth
Seasons one to four, six and nine each ran 24 episodes.
Q 14Ashton Kutcher's character Walden Schmidt is what?
An Internet billionaire
He tells Alan at Pavlov's bar that he made $1.3 billion by selling his website to Microsoft.
Q 15According to Rose in the season nine premiere, how did Charlie Harper die?
Hit by a Paris Metro train
She hints she pushed him after catching him cheating; the finale later reveals she had actually imprisoned him.
Q 16How many viewers watched Kutcher's 2011 debut episode 'Nice to Meet You, Walden Schmidt'?
28.7 million
Nielsen called it the highest-rated episode since the series began.
Q 17Which actor played Charlie's ghost in the episode 'Why We Gave Up Women'?
Kathy Bates
The ghost is spending eternity in hell as a woman with a pair of testicles.
Q 18Which relative of the original star played Rose's equally disturbed father, Harvey?
Martin Sheen
His brother Emilio also appeared, as an old friend of Charlie's.
Q 19Ashton Kutcher's real-life partner appeared as Walden's love interest in season 11. Who?
Mila Kunis
They were engaged at the time and married later.
Q 20What was the name of the show's 100th episode, aired October 15, 2007?
City of Great Racks
Warner Bros. marked it by handing the crew blue Micargi bicycles and Tiffany key rings.
Q 24Which church did Angus T. Jones say he had joined when he called the show 'filth' in a 2012 interview?
Seventh-day Adventist
He apologised the next day, later called himself 'a paid hypocrite', and left after season 10.
Q 25After leaving the beach house, Jake joins which organisation?
The US Army
He serves as a chef, then announces he is being posted to Japan for a year.
Q 26What alias does the billionaire adopt when he pretends to be poor while dating Kate?
Sam Wilson
He wants someone who loves him for himself; the money still ends up launching Kate's fashion career.
Q 27What fake name does Alan use to spy on Lyndsey's new boyfriend Larry?
Jeff Strongman
The double life gets messy when 'Jeff' starts dating Larry's sister Gretchen.
Q 28Who plays Jenny, Charlie's long-lost daughter, introduced in season 11?
Amber Tamblyn
She turns out to share her father's taste for alcohol and women.
Q 29In the final season, why do Walden and Alan get married?
So they can adopt a child
They adopt six-year-old Louis and then divorce to chase women again.
Q 30What was the title of the two-part 2015 series finale?
Of Course He's Dead
The title itself was a tease about whether Sheen would return.