It's a trivia quiz. @NKraft @dev
  1. tennis player OR musician
  2. 41 OR 43
  3. conquistador OR auteur
  4. naval fighter OR drummer
  5. Space Jam OR The Wire
  6. forgotten founder OR watermarked business card
  7. Irish OR astronaut
  8. basketball coach OR train driver OR TMNT
  9. running back OR running back
  10. right fielder OR treasury secretary
    Since this one is hard: played for Reds and Yankees and won 5 World Series. Was chairman of Alcoa.
  11. Brokeback Mountain OR Destiny's Child
  12. Bonus round: Famous pop star OR almost famous groupie
  13. Oscar nominated director (2013) or Oscar nominated actor (1967)
    Suggested by @davidkwong