Through the (Penta) years

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Across
  1. 3. The sharing feline released in 1999
  2. 7. AdMob: $750 million in 2009, to this highest bidder
  3. 8. How Toyota says luxury, starting in 1989
  4. 9. New territory up north in 1999
  5. 11. Colorful book released in 1999. Don't forget to plug it in.
  6. 12. In which the Lady isn’t a cheerleader, but says ‘rah-rah’ all the same (2009 hit single)
  7. 13. Our 2009 EOYP locale; Eloise didn’t crash
  8. 16. Gambler's paradise; returned from Portugal in 1999
  9. 17. Chinese square, made infamous in 1989
  10. 18. DESCO's 2004 skylight?
  11. 21. Comrade General Secretary for short, in 1989
  12. 23. Bey, were she a 2009 spy
  13. 24. One of Mars' permanent visitors, with a 2004 arrival
  14. 30. His light in the attic was turned off for good in 1999
  15. 31. She turned 40 in 1999, probably in her Malibu dreamhouse
  16. 32. This city’s Tribune couldn’t handle its debt tribulations in 2009
  17. 35. 1989 oil streak perpetrator
  18. 36. The year's most monstrous actress in 2004
  19. 39. DESCO's 2004 playdate prtnr. first name; founded by the brothers Kaufman
  20. 40. The firmest group of Poles around in 1989
  21. 42. Coffee for techies, released in '94
  22. 44. 1994 trade Agmt. uniting a continent
  23. 45. Cup org.; Brazil foots it in 1994
  24. 46. 2004 winner of the golden, yet rotten, raspberry
  25. 49. Philosopher launched in 1989
  26. 51. We’ve been looking for her and her red trench coat since 1994
  27. 54. 1989 ozone conference locale
  28. 56. The Old World's new 1999 currency
  29. 57. Mr. Democrat of 2004; John ______
Down
  1. 1. Ancient and modern spíti of the Games, in 2004 at least
  2. 2. TV's funniest working-class lady in 1989
  3. 4. Carbon and iron alloy city bowlers in 2009
  4. 5. 2004 Ukraine's favorite revolutionary fruit
  5. 6. A vodka mister, swimming in world records in 1994
  6. 10. New kōtei in 1989
  7. 12. Russia's drunkest politico; resigned in 1999
  8. 14. Humans as alien invaders (2009 blockbuster)
  9. 15. A steel bird ended its days in this river in 2009
  10. 19. White-collar crime's most ‘authentic’ celebrity of 2004
  11. 20. Chocolate rapper; produced Mr. Shady in 1999
  12. 22. Apparently this horse didn't gallop fast enough for Homer's same-surname figure
  13. 25. Batar daan-makers, but not since 1999
  14. 26. Paramount Pretoria Politico in 1999
  15. 27. Words excel in this 1989 software release
  16. 28. Newest Japanese player in 1989
  17. 29. Playing in the Forrest in '94 really paid off for him
  18. 33. 2004 Jeopardy expert
  19. 34. Famous political rationalizer of ‘99: ‘Is “is”?’
  20. 37. How it felt for Madonna when you called her name in 1989
  21. 38. Netflix-original namesake town; '94 chilly competition locale
  22. 41. Ms. _______ ‘barred’ in ‘94 from all future skating competitions
  23. 43. Hippie's haven so nice they recreated it twice (in '94 and '98)
  24. 46. Google's 2004 April Fool's joke? Check your inbox!
  25. 47. Not an Amazon woman, but a DESCO man 'til '94
  26. 48. Sweeney Todd dame name elected to Icelandic office in 2009
  27. 50. Greek letter magazine featuring our big six in 2009
  28. 52. 107 years of work, ending in 2004, made this moto-maker particularly Old
  29. 53. 1 of 5; died in 2009. Michael ______
  30. 55. Stanley certainly favored them in 1994