This Tax Day trivia quiz has 50 free questions with answers and covers the April 15 deadline and how it got there, from Lincoln's Civil War income tax and the Sixteenth Amendment to Form 1040, e-filing, Emancipation Day extensions and the pandemic postponements. Then it goes wider: Al Capone, Wesley Snipes and Leona Helmsley's little people; the Boston Tea Party and Stamp Act; England's window and hat taxes, Peter the Great's beard tax, Gandhi's Salt March and Lady Godiva; and modern oddities like the jock tax, Denmark's fat tax and the tampon tax. It works as an office icebreaker on filing day or as a history round for a trivia night. The first questions are easy; the last few will stretch accountants. Every question is multiple choice with a short explanation after you answer. Every answer has been checked against a primary source, and each question links to the page that confirms it.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Since 1955, US Tax Day has typically fallen on or just after which date?
April 15
It moves when the date hits a weekend or Emancipation Day in Washington, DC.
Q 02When federal income tax began in 1913, what was the filing deadline?
March 1
It moved to March 15 in 1918 and to April 15 in 1955.
Q 03Which amendment, ratified in 1913, let Congress tax incomes without apportioning by state population?
Sixteenth
It overturned the Supreme Court's 1895 Pollock decision, which had struck down an earlier income tax.
Q 04Which 1895 Supreme Court case struck down the federal income tax?
Pollock v. Farmers' Loan & Trust
The Court ruled that unapportioned taxes on interest, dividends and rents were effectively direct taxes.
Q 05The first US federal income tax was introduced in 1861 to fund what?
The Civil War
It was a flat 3% on incomes above $800, signed by Abraham Lincoln.
Q 06What was the rate of the 1861 income tax on incomes above $800?
3%
The 1862 Act replaced the flat rate with a progressive scale of 3% and 5%.
Q 07The IRS traces its origin to the Office of Commissioner of Internal Revenue, created in which year?
1862
The wartime income tax funded over a fifth of the Union's war costs before it lapsed a decade later.
Q 08In 1953 the federal tax bureau adopted the name it still uses. What is it?
Internal Revenue Service
The IRS collects roughly 96% of the federal government's operational funding.
Q 09Why is the main US individual tax return numbered 1040?
It was the next form number in sequence
The first 1040, for tax year 1913, was three pages and 31 lines long.
Q 10Which two simplified versions of the main individual tax return were dropped for tax year 2018?
1040-A and 1040-EZ
Six new schedules were split out that year to make parts of the main form optional.
Q 11Limited electronic filing of US tax returns first became possible in which year?
1986
The 1998 Restructuring Act later reorganised the IRS into four operating divisions.
Q 12Tax Day is pushed back when April 15 collides with which Washington, DC holiday?
Emancipation Day
Because the IRS observes DC holidays, the whole country gets the extension.
Q 13In which year did Lincoln sign the April 16 act freeing about 3,100 enslaved people in the District of Columbia?
1862
It freed about 3,100 people in the District nine months before the Emancipation Proclamation.
Q 21Benjamin Franklin's 'nothing is certain except death and taxes' came in a 1789 letter about what?
The newly established Constitution
Earlier versions appear in Defoe (1726) and Christopher Bullock's The Cobbler of Preston (1716).
Q 22The all-time-high US top marginal income tax rate of 94% applied during which years?
1944-1945
It hit incomes above $200,000; the top rate was still 92% in 1952-53.
Q 23As of 2023, how many US states imposed a state income tax?
42
New Hampshire then taxed only interest and dividends; it repealed that tax from 2025. Payroll taxes for Social Security and Medicare are levied on wages regardless of state.
Q 14Which New England holiday has occasionally given Maine and Massachusetts filers an extra day?
Patriots' Day
Post offices in those states are closed on the day.
Q 15In 2020 the federal filing deadline was pushed to which date because of the COVID-19 pandemic?
July 15
In 2021 it moved again, to May 17.
Q 16Al Capone was finally jailed in 1931 for what crime?
Tax evasion
He was convicted on five of twenty-two counts and sentenced to eleven years.
Q 17How long was Al Capone's 1931 federal prison sentence?
Eleven years
He was moved to the newly opened Alcatraz in August 1934.
Q 18Actor Wesley Snipes was convicted in 2008 of what tax offence?
Willful failure to file returns
The misdemeanor convictions brought a three-year sentence; he served 28 months.
Q 19Hotelier Leona Helmsley was reported to have said that only whom pay taxes?
The little people
The 'Queen of Mean' served 19 months and later left $12 million to her dog, Trouble.
Q 20Leona Helmsley's will originally left how much to her Maltese dog, Trouble?
$12 million
A court cut it to $2 million as excessive; Fortune ranked it among 2007's dumbest business moments.
Q 24Who invented 'Tax Freedom Day' in 1948?
Businessman Dallas Hostetler
He trademarked the phrase and handed it to the Tax Foundation on retiring in 1971.
Q 25The Boston Tea Party of December 1773 destroyed roughly how many chests of tea?
342
The Sons of Liberty, some dressed as Mohawks, dumped about 92,616 pounds of tea into the harbour.
Q 26Britain's Stamp Act of 1765 taxed which colonial goods?
Printed paper and playing cards
The tax had to be paid in British currency and was repealed in March 1766.
Q 27England's window tax, blamed for bricked-up windows, was introduced in 1696 and repealed in which year?
1851
France had a similar tax from 1798 to 1926.
Q 28Which Russian ruler introduced a beard tax in 1698 to westernise his subjects?
Peter the Great
Payers carried a copper 'beard token'; Catherine the Great repealed the tax in 1772.
Q 29Roughly how far did Gandhi walk to Dandi on the 1930 Salt March?
240 miles
He set out with 78 volunteers on a 24-day march and made salt by evaporation on 6 April.
Q 30Legend says Lady Godiva rode naked through which English city to win a tax cut for its people?
Coventry
'Peeping Tom' comes from later versions, in which a man named Thomas watched and was struck blind.