41 Presidential Jokes: The 1998 “Starr Reports & Blue Dresses” Edition

In 1998, the American Presidency became the world’s most-watched soap opera. It was the year of “The Finger Wag,” the 445-page report that crashed government servers, and the realization that the “Information Superhighway” was perfect for spreading gossip at the speed of light.

The 1998 Executive Top 10: “Subpoenas & Scandals”

1. The Definition of “Is”: Why did the President become a linguist in 1998? Because he realized that winning an election is easy, but explaining the tense of a single verb to a Grand Jury is a marathon.
2. The Kenneth Starr Bestseller: Why was the Starr Report the most popular download of 1998? Because it was the first time the government provided “Adult Content” without a credit card requirement.
3. The “I Did Not Have Sexual Relations” Speech: Why was the 1998 finger-wag so famous? Because the President’s finger was the only part of the administration that stayed “on message” that day.
4. The Monica Lewinsky Internship: Why was 1998 a bad year for White House resumes? Because suddenly, “Internship at the West Wing” required more explaining than a gap year in a cult.
5. The Blue Dress Legacy: Why was the Gap so nervous in 1998? Because they never expected one of their dresses to become a key piece of “State Evidence.”
6. The Google Launch: Why did Google start in 1998? Because Larry Page and Sergey Brin realized people needed a faster way to search for “What is an Independent Counsel?”
7. The Impeachment Vote: Why was the House of Representatives like a courtroom in ’98? Because the Republicans decided that if they couldn’t beat Clinton on the economy, they’d try to beat him on the “Moral Economy.”
8. The Viagra Approval: Why did the FDA approve Viagra in 1998? To give the late-night talk show hosts enough material to survive the rest of the Clinton presidency.
9. The Armageddon vs. Deep Impact: Why were there two asteroid movies in 1998? Because the American public felt that a giant rock hitting Earth was less stressful than watching the evening news from Washington.
10. The Frank Sinatra Passing: Why was the White House so sad when Ol’ Blue Eyes died? Because even the President knew that “My Way” was getting a lot harder to sing under oath.

The Full 1998 Presidential Jokes Archive

11. The Grand Jury Testimony: Why did the President wear a tie with a hidden meaning? Because in 1998, even his silk accessories were suspected of being “co-conspirators.”
12. The “Vast Right-Wing Conspiracy”: Why did Hillary coin that phrase? Because “They’re out to get us” sounded too much like a movie plot, and “Conspiracy” sounded more like a political fundraiser.
13. The Savings & Loan Legacy: Why was 1998 so expensive? Because the only thing growing faster than the surplus was the legal bill for the Executive Branch.
14. The Titanic Oscar Sweep: Why did Clinton relate to the movie Titanic (again)? Because in ’98, he felt like the captain, the band, and the iceberg all at the same time.
15. The Newt Gingrich Resignation: Why did the Speaker leave in 1998? Because he realized that throwing stones in a glass house is fine until the house starts throwing subpoenas back.
16. The Operation Desert Fox: Why did the President order airstrikes in December? Because nothing says “Merry Christmas” and “Please stop talking about the impeachment” like a precise military operation.
17. The Furby Craze: Why did the White House ban Furbies? Because the Secret Service was afraid the toys would learn more state secrets than the interns.
18. The Exxon-Mobil Merger: Why did the oil giants merge? To prove that in 1998, even corporations wanted a “partner” to help handle the heat.
19. The Seinfeld Finale: Why was the President jealous of Jerry Seinfeld? Because Jerry got to go to jail for “Doing Nothing,” while Bill was in trouble for doing… well, something.
20. The Good Will Hunting Success: Why did the President like the movie? Because he also spent the year trying to prove he was a “Genius” while everyone else focused on his “Rough Neighborhood” habits.
21. The iMac G3 Release: Why did the White House get the colorful iMacs? To make the “Deposition Videos” look a little more cheerful.
22. The John Glenn Space Return: Why did a 77-year-old go back to space? To get as far away from the Washington press corps as humanly possible.
23. The Good Friday Agreement: Why was this Bill’s best day of ’98? Because “Peace in Ireland” was the only headline that didn’t involve a dress or a cigar.
24. The Drudge Report Power: Why was Matt Drudge so feared? Because in 1998, a guy in a hat with a modem had more “Breaking News” than the entire New York Times.
25. The Midterm Election Surprise: Why were the Democrats happy in November? Because the American public looked at the scandal, looked at their 401(k)s, and decided they liked money more than morality.
26. The Linda Tripp Tapes: Why was 1998 the year of the “Record” button? Because everyone learned that your “Best Friend” might just be a freelance court reporter.
27. The Wag the Dog Movie: Why was this film so awkward in 1998? Because it was the first time a Hollywood satire turned into a C-SPAN documentary.
28. The Mark McGwire vs. Sammy Sosa: Why did the President love the Home Run race? Because it was the only “Internal Investigation” that involved actual baseballs.
29. The Lewinsky “Talking Points”: Why were they so controversial? Because in Washington, “Writing it down” is the second-worst thing you can do, right after “Saying it out loud.”
30. The Vernon Jordan Role: Why was the President’s friend so busy? Because being a “fixer” in 1998 was a 24-hour job that didn’t include health benefits.
31. The Saddam Hussein Standoff: Why was Iraq back in the news? Because some things in the 90s never went out of style—like flannel shirts and Middle East crises.
32. The Microsoft Antitrust Suit: Why was Bill Gates in court too? Because 1998 was the year the government decided that being “Too Successful” was a crime—unless you were the guy in the Oval Office.
33. The Saving Private Ryan Premiere: Why was it a hit in D.C.? Because every politician wanted to be seen “Honoring the Past” to avoid talking about the “Present.”
34. The White House Easter Egg Roll: Why was it tense? Because the Secret Service treated every chocolate bunny like it was wearing a wire.
35. The Britney Spears Debut: Why was “…Baby One More Time” the song of the year? Because the President’s legal team kept asking the Grand Jury for “One More Time” to explain the testimony.
36. The “Perjury” Debate: Why was the word so popular? Because it’s a much fancier way of saying “Oops, I forgot the truth.”
37. The Tobacco Master Settlement: Why did the states get $206 billion? Because the only thing more addictive than nicotine in 1998 was suing someone for it.
38. The European Central Bank: Why was it formed? Because Europe wanted a “Single Currency” to avoid the “Double Standards” of American politics.
39. The “Executive Privilege” Claim: Why did the President use it so much? Because “Mind Your Own Business” isn’t a valid legal defense in the Constitution.
40. The Y2K Panic Growth: Why were people buying canned food? Because after 1998, everyone assumed that if the government couldn’t handle a scandal, it definitely couldn’t handle a calendar change.
41. The Final 1998 Vibe: Why was it a “Surreal” year? Because the President was impeached, the stock market hit 9000, and the American people just wanted to go home and watch Sex and the City.