We've been running trivia quizzes in some form since about 2000. Back then, a question like "What song popularized the phrase Heavy Metal?" was a good stumper. But over the next several years those questions got really easy to look up, so we had to get creative. Here are 10 of our most challenging questions that you probably won't be able to look up.
1) What number greater than 10 shows up in the titles of the most US Top 40 hits?Show Answer
16, usually in reference to the age:"Sweet Little Sixteen" - Chuck Berry (1958)
"Only Sixteen" - Sam Cooke (1959), Dr. Hook (1976)
"Sixteen Reasons" - Connie Stevens (1960)
"Happy Birthday, Sweet Sixteen" - Neil Sedaka (1962)
"You're Sixteen" - Johnny Burnette, Ringo Starr (1974)
"Christine Sixteen" - Kiss (1977)
"Sweet Sixteen" - Billy Idol (1986)
"Summer Sixteen" - Drake (2016)
2) What fruit shows up in the lyrics to hits by Def Leppard, Prince, Steve Miller and Ringo Starr?Show Answer
Peaches:Def Leppard - "You got the peaches I got the cream" ("Pour Some Sugar On Me")
Prince - "Color you peach and black, color me taken aback" ("U Got the Look")
Steve Miller: "Really love your peaches want to shake your tree" ("The Joker")
Ringo Starr - "You come on like a dream peaches and cream" ("You're Sixteen")
3) Who had Top 40 hits with covers of songs by The Beatles, The Rolling Stones and Simon & Garfunkel?Show Answer
Aretha Franklin:"Eleanor Rigby" (#17, 1969)
"Jumpin' Jack Flash" (#21, 1986)
"Bridge Over Troubled Water" (#6, 1971)
4) Which actor who died in the '50s is mentioned in three of the most famous songs of the '70s?Show Answer
James Dean. He shows up in:"Walk On The Wild Side" by Lou Reed:
Jackie is just speeding away
Thought she was James Dean for a day
"Rock On" by David Essex:
See her shake on the movie screen
Jimmy Dean (James Dean)
"American Pie" by Don McLean:
The jester sang for the king and queen
In a coat he borrowed from James Dean
5) Since 1960, what's the only #1 Hot 100 hit recorded outdoors to a live audience?Show Answer
"Don't Let The Sun Go Down On Me" by Elton John and George Michael.The pair sang it at Wembley Arena in London in 1991. Released as a single, it went to #1 in America and the UK.
6) Besides Heart and Wilson Phillips, what band with two sisters in the group had two #1 Hot 100 hits?Show Answer
The Bangles: "Walk Like An Egyptian" and "Eternal Flame." Vicki and Debbi Peterson are the sisters in that group.7) Before Adam Sandler, what comedian debuted a hit song on Saturday Night Live?Show Answer
Steve Martin with "King Tut" in 1978.8) What Rock and Roll Hall of Fame band's highest charting hit (Hot 100) is a cover of a song from the '60s?Show Answer
Pearl Jam. "Last Kiss," originally by J. Frank Wilson And The Cavaliers in 1964, went to #2 for PJ in 1999. It was held out of #1 by J. Lo's first single, "If You Had My Love."9) What famous singer always opens his/her concerts with the same cover song?Show Answer
Willie Nelson. His opening number is always a cover of "Whiskey River" by Johnny Bush.10 What hit song has the word "pink" in the lyric, but a different color in the title?Show Answer
"Big Yellow Taxi" by Joni Mitchell:They paved paradise
And put up a parking lot
With a pink hotel, a boutique
And a swinging hot spot
June 9, 2025
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