Criteria: - These songs were ranked based on influence, popularity, innovation, critical acclaim, and overall quality of music. Each song demonstrates a deviation from the normal subject matter/approach/aesthetic/themes of hip-hop music at any given time.
http://digitaldreamdoor.com/pages/best_ ... songs.html

1. Outkast - B.O.B.
2. Gnarls Barkley - Crazy
3. De La Soul - Me, Myself & I
4. Arrested Development - Tennessee
5. The Pharcyde - Passin' Me By
6. A Tribe Called Quest - Can I Kick It?
7. Digable Planets - Rebirth of Slick (Cool Like Dat)
8. The Fugees - Ready or Not
9. Beastie Boys - Sure Shot
10. Busta Rhymes - Put Your Hands Where My Eyes Can See
11. PM Dawn - Set Adrift on Memory Bliss
12. Queen Latifah - Unity
13. Gorillaz - Feel Good Inc.
14. Digital Underground - The Humpty Dance
15. A Tribe Called Quest - Scenario
16. Gang Starr - Mass Appeal
17. Jungle Brothers - What U Waitin' 4
18. Stetsasonic - Talkin' All That Jazz
19. Outkast - Hey Ya!
20. Missy Elliot - The Rain (Supa Dupa Fly)
21. US3 - Cantaloop (Flip Fantasia)
22. MIA - Paper Planes
23. The Roots - What They Do
24. De La Soul - Breakadawn
25. Lauryn Hill - Doo Wop (That Thing)
26. Black Sheep - The Choice is Yours
27. Del the Funkee Homosapien - Mistadobalina
28. Beastie Boys - Intergalactic
29. Common - I Used to Love H.E.R.
30. The Pharcyde - Drop
31. Talib Kweli - Get By
32. Arrested Development - Mr. Wendal
33. Fatlip - What's Up Fatlip?
34. Wyclef Jean - Gone Til November
35. Busta Rhymes - Gimme Some More
36. A Tribe Called Quest - Award Tour
37. The Fugees - Fu-Gee-La
38. Outkast - Ms. Jackson
39. Beastie Boys - So What'cha Want
40. Jurassic 5 - What's Golden
41. Gorillaz - Clint Eastwood
42. KRS-One - MC's Act Like They Don't Know
43. De La Soul - A Rollerskating Jam Called "Saturdays"
44. Lupe Fiasco - Kick, Push
45. Brand Nubian - 360 Degrees (What Goes Around)
46. Leaders of the New School - The International Zone Coaster
47. Ultramagnetic MC's - Ego Trippin'
48. Q-Tip - Vivrant Thing
49. Beastie Boys - Hey Ladies
50. Dilated Peoples - This Way
51. Mos Def - Universal Magnetic
52. Outkast - Rosa Parks
53. Stetsasonic - Just Say Stet
54. The Pharcyde - Otha Fish
55. The Roots - The Seed 2.0
56. Jungle Brothers - I'll House You
57. Black Star - Definition
58. Little Brother - Lovin' It
59. A Tribe Called Quest - Check the Rhime
60. Common - Testify
61. Gang Starr - Take It Personal
62. Arrested Development - People Everyday
63. Talib Kweli - Good to You
64. Gnarls Barkley - Smiley Faces
65. Del the Funky Homosapien - If You Must
66. Jurassic 5 - Quality Control
67. Queen Latifah - Just Another Day
68. The Pharcyde - Runnin'
69. De La Soul - Potholes on My Lawn
70. The Roots - You Got Me
71. Busta Rhymes - Woo Hah!! Got You All in Check
72. Aesop Rock - Daylight
73. Mos Def - Umi Says
74. Lauryn Hill - Everything is Everything
75. El-P - Stepfather Factory
76. Atmosphere - Modern Man's Hustle
77. Q-Tip - Breathe and Stop
78. Beastie Boys - Ch-Check It Out
79. MIA - Galang
80. cLOUDDEAD - Dead Dogs Two
81. Nappy Roots - Po' Folks
82. Slum Village - Raise it Up
83. Dilated Peoples - Worst Comes to Worst
84. The Roots - Stay Cool
85. Gnarls Barkley - Run (I'm A Natural Disaster)
86. Lupe Fiasco - Daydreamin'
87. De La Soul - Ring Ring Ring (Ha Ha Hey)
88. The Alkaholiks - Make Room
89. Kid Cudi - Day 'n' Nite
90. Missy Elliot - Sock It 2 Me
91. Goodie Mob - Cell Therapy
92. Eyedea & Abilities - Blindly Firing
93. Aesop Rock - None Shall Pass
94. P.O.S. - Drumroll (We're All Thirsty)
95. Gorillaz - Rock the House
96. Outkast - Elevators (Me & You)
97. MC Lars - iGeneration
98. Little Brother - The Get Up
99. Digable Planets - 9th Wonder (Blackitolism)
100. Channel Live - Mad Izm

(see above for list)

Good list!

this is gonna be my go-to thread

I would like to know why "B.O.B." is #1 when it is not even the greatest Outcast song. Maybe I am missing something about it, would you mind educating me please?

It's their second most acclaimed song, only to 'Hey Ya'

Should't Madvillain and MF Doom be on here?

But acclaim is only one part of criteria. What about influence, innovation,etc. And there are songs on this list more popular than "B.O.B." So what makes it #1?

Hey, I didn't make the list, im just giving the most understandable answer for it being number one. I don't think it should be number one, either.