Madonna’s 23 Most Cringe-Worthy Moments

Truth: We all miss Madonna, circa 1988. Dare: Make it through this page without cringing. (An ode to Truth or Dare - a fragrance by Madonna.)

23. That time she found her high school cheerleading uniform.

22. That time she was hangin with Bob Ross.

21. That time she took up yoga…

20. …and then decided…

19. “These would be killer dance moves.”

18. That time she didn’t know how beds work.

17. That time she didn’t understand floors.

16. That time she pulled a hamstring.

15. That time she was up in da club.

14. That time she joined Instagram.

13. That time wore her hair up.

12. That time she didn’t regret her corn rows.

11. That time she was blingin.

10. That time she pumped too much iron.

9. That time she had terrible posture.

8. That time she taught us about natural childbirth.

7. That time someone gave her flowers.

6. That time she sold ladies pocketbooks.

“People spend $300 on crazy things all the time — things like handbags. So work all year, scrape the money together, and come to my show. I’m worth it.”

5. That time she was really bad at haikus.

4. That time she asked will.i.am for a favor.

3. That time she told us about how Tom has it really really rough, you guys!

“Tom [Cruise] is a good person. I think he gets a raw deal, just as I think the orphans in Malawi get a raw deal; just as I think a lot of marginalized people get a raw deal.”

2. That time she actually didn’t help anything at all.

1. Oh yeah - and that time she was British.

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