1. Venus Williams
2. Serena Williams
3. Naomi Osaka
4. Maria Sharapova
5. Michelle Wie
6. Tara Lipinski
7. Michelle Kwan
8. Kim Yuna
9. Mary Lou Retton
10. Simone Biles
11. Aly Raisman
12. Shawn Johnson
13. Mia Hamm
14. Abby Wambach
15. Brittany Griner (edit: should be Brittney)
16. Nastia Liukin
17. Eleanor Roosevelt
18. Patricia Nixon
19. Jackie Kennedy
20. Nancy Reagan
21. Hillary Clinton
22. Madeline Albright
23. Margaret Thatcher
24. Liz Truss
25. Angela Merkel
26. Laura Bush (not counting Michelle Obama because she's in the prompt)
27. Melania Trump
28. Ivanka Trump (edit: Tiffany forever forgotten lmao)
29. Jill Biden
30. Elizabeth Warren
31. Amy Klobuchar
32. Marianne Williamson
33. Kyrsten Sinema
34. Marjorie Taylor-Green (edit: should be Taylor Greene)
35. Alexandria Ocasio-Cortez
36. Tammy Duckworth
37. Nancy Pelosi
38. Dianne Feinstein (rest in piss)
39. Rashida Tlaib
40. Rashida Jones
41. Ilhan Omar
42. Barbara Boxer
43. Barbra Streisand
44. Barbara Bush
45. Emma Watson
46. Charlotte Brontë
47. Emily Brontë (sorry other Brontë sister I forgot your name WH OMEGALUL)
48. Jane Austen
49. Ursula K. Le Guin
50. J.K. Rowling (ugh)
51. Maggie Gyllenhall (edit: should be Gyllenhaal)
52. Cate Blanchett
53. Kiera Knightley (I definitely misspelled her name) (edit: FUCK I HAD IT RIGHT THE FIRST TIME AND THEN CHANGED IT)
54. Mila Kunis
55. Sandra Bullock
56. Monica Lewinsky
57. Meryl Streep
58. Amy Adams
59. Lindsay Lohan
60. Britney Spears
61. Paris Hilton
62. Christina Aguilera
63. Mariah Carey
64. Whitney Houston
65. Aretha Franklin
66. Diana Ross
67. Patti LaBelle
68. Donna Summer
69. Gloria Gaynor
70. Chaka Khan
71. Jennifer Hudson
72. Ariana Grande
73. Etta James
74. Ella Fitzgerald
75. Diana Krall
76. Doris Day
77. Ginger Rogers
78. Judy Garland
79. Audrey Hepburn
80. Coco Chanel
81. Elizabeth Hurley (I was trying to remember Elizabeth Taylor but blanked on the last name) (not counting Marilyn Monroe because she's in the prompt)
82. Rosemary Clooney
83. Bette Davis
84. Betsy Ross
85. Harriet Tubman
86. Rosa Parks
87. Rosa Luxemburg
88. Angelina Jolie
89. Park Geun-hye (disgraced South Korean president)
90. Jennifer Lopez
91. Beyoncé Knowles
92. Kelly Rowland
93. Taylor Swift (just squeaked in there!)
94. Stevie Nicks
95. Courtney Love
96. Celine Dion
97. Avril Lavigne
98. Miranda Cosgrove
99. Oprah Winfrey
100. Jennifer Aniston

1 through 16 are athletes:

• 1-4: tennis
• 5: golf
• 6-8: figure skating
• 9-12 + 16: gymnastics
• 13-14: football/soccer
• 15: basketball

17-21, 26, 27, 29, 44 are First Ladies of the United States (28 (Ivanka) is a daughter of a president)

22-25, 30-39, 41-42, 89 are various politicians (nearly all Americans with a few Br*ts, a German, and a South Korean)

40, 45, 51-55, 57-59, 77, 79, 81, 83, 88, 98, and 100 are actors (I'm not double counting people like Doris Day or Judy Garland)

46-50 are authors (couldn't remember Shelley's first name)

56 is Monica Lewinsky...not really sure what made me think of her at this point tbh

61 (Paris Hilton) is the lone "pure celebrity" on the list I think

43, 60, 62-76, 78, 82, 90-97 are singers (with some double- and triple-threats in there), going from 00s pop to divas to jazz to midcentury Hollywood and then a jumble at the very end

80 (Coco Chanel) is a fashion designer

84-87 are various historical figures

99 (Oprah Winfrey) is a TV host/billionaire mogul

Numbers by category:

27 singers

17 politicians

17 actors

16 athletes

9 FLOTUSes

5 authors

2 civil rights icons

1 flagmaker

1 president's daughter

1 doomed socialist

1 reality star

1 woman who was treated horrifically by the media (not that others on this list weren't, but that's what she's known for)

1 fashion designer

1 TV host/billionaire