Maybe you could have Jesse Venture run instead?
Ventura never got into politics in this timeline because he was the leader of WAG in the early 90's and never ran for mayor.
List of Billboard #1 songs for 2008
940: Low - Flo Rida ft. T-Pain (January 5 - February 23, 2008)
941: Don't Stop The Music - Rihanna (March 1 - March 29, 2008)
942: Stop and Stare - OneRepublic (April 5, 2008)
943: Touch My Body - Mariah Carey (April 11 - April 19, 2008)
944: Bleeding Love - Leona Lewis (April 26; May 10 - May 17, 2008)
945: Lollipop - Lil Wayne ft. Static Major (May 3, 2008)
946: Viva La Vida - Coldplay (May 24 - June 28)
947: I Kissed A Girl - Katy Perry (July 5 - July 19, 2008)
948: A Milli - Lil Wayne (July 26 - August 16, 2008)
949: Disturbia - Rihanna (August 23 - August 30, 2008)
950: Paper Planes - M.I.A (September 6 - September 20, 2008)
951: So What - P!nk (September 27, 2008)
952: Whatever You Like - T.I (October 4 - October 11, 2008)
953: Human - The Killers (October 18 - October 25, 2008)
954: Let It Rock - Kevin Rudolf ft. Lil Wayne (November 1 - November 8, 2008)
955: Live Your Life - T.I ft. Rihanna (November 15 - December 6, 2008)
956: Single Ladies - Beyoncé (December 13 - December 27, 2008)
Billboard 2008 Year End List
1. Low - Flo Rida ft. T-Pain
2. No One - Alicia Keys
3. Paralyzer - Finger Eleven
4. I Kissed A Girl - Katy Perry
5. Viva La Vida - Coldplay
6. Disturbia - Rihanna
7. Whatever You Like - T.I
8. Apologize - Timbaland ft. OneRepublic
9. Bleeding Love - Leona Lewis
10. Closer - Ne-Yo
11. Touch My Body - Mariah Carey
12. No Air - Jordan Sparks ft. Chris Brown
13. So What - P!nk
14. Burnin' Up - Jonas Brothers
15. Don't Stop The Music - Rihanna
16. Let It Rock - Kevin Rudolf ft. Lil Wayne
17. Paper Planes - M.I.A
18. Love in This Club - Usher
19. Live Your Life - T.I ft. Rihanna
20. Pocketful of Sunshine - Natasha Bedingfield
21. 4 Minutes - Maddona ft. Justin Timberlake and Timbaland
22. Stop and Stare - OneRepublic
23. With You - Chris Brown
24. Flux - Bloc Party
25. Clumsy - Fergie
26. I'm Yours - Jason Mraz
27. Leavin' - Jesse McCarthy
28. Lucid Dreams - Franz Ferdinand
29. A Milli - Lil Wayne
30. See You Again - Miley Cyrus
31. Shake It - Metro Station
32. Take You There - Sean Kingston
33. Hot n' Cold - Katy Perry
34. Something That's Long Gone - Rainbow Rebels
35. Like You'll Never See Me Again - Alicia Keys
36. Teardrops on My Guitar - Taylor Swift
37. Shadow Of The Day - Linkin Park
38. Lollipop - Lil Wayne ft. Static Major
39. Forever - Chris Brown
40. Miss Independent - Ne-Yo
41. Good Life - Kanye West ft. T-Pain
42. In The Ayer - Flo Rida ft. will.i.am
43. Say - John Mayer
44. Human - The Killers
45. Can't Believe It - T-Pain ft. Lil Wayne
46. Crank That - Soulja Boy Tell 'Em
47. Superstar - Lupe Fiasco ft. Matthew Santos
48. Big Girls Don't Cry - Fergie
49. Suffocate - J. Holiday
50. Hate That I Love You - Rihanna ft. Ne-Yo
51. Love Lockdown - Kanye West
52. It's Not My Time - 3 Doors Down
53. Sexy Can I - Ray J ft. Yung Berg
54. Get Like Me - David Banner ft. Chris Brown and Yung Joc
55. Put On - Young Jeezy ft. Kanye West
56. Hypnotized - Plies ft. Akon
57. Big Ideas - LCD Soundsystem
58. When I Grow Up - Pussycat Dolls
59. Sexual Eruption - Snoop Dogg
60. Lolli Lolli - Three 6 Mafia
61. Cyclone - Baby Bash ft. T-Pain
62. What You Got - Colby O'Donis ft. Akon
63. Independent - Webbie ft. Lil Boosie and Lil Phat
64. Crush - David Archuleta
65. New Soul - Yael Naim
66. In Love With a Girl - Gavin DeGraw
67. Dangerous - Kardinal Offishal ft. Akon
68. I Luv Your Girl - The-Dream ft. Young Jeezy
69. Womanizer - Britney Spears
70. Love Story - Taylor Swift
71. Just Fine - Mary J. Blidge
72. Piece of Me - Britney Spears
73. Can't Help but Wait - Trey Songz
74. My Life - The Game ft. Lil Wayne
75. 7 Things - Miley Cyrus
76. You're Gonna Miss This - Trace Adkins
77. Love Remains the Same - Gavin Rossdale
78. Feels Like Tonight - Daughtry
79. The Way I Are - Timbaland ft. Keri Hilson
80. Addicted - Saving Abel
81. I'll Keep Your Memory Vague - Finger Eleven
82. Love Song - Sarah Bareilles
83. Bad Girlfriend - Theory of a Deadman
84. American Boy - Estelle ft. Kanye West
85. Sorry - Buckcherry
86. Tattoo - Jordin Sparks
87. Beat It - Fall Out Boy ft. John Mayer
88. The Day That Never Comes - Metallica
89. Bust It Baby - Plies ft. Ne-Yo
90. Sun Goes Down - David Jordan
91. All Summer Long - Kid Rock
92. Our Song - Taylor Swift
93. Damaged - Danity Kane
94. Single Ladies - Beyoncé
95. Mercury - Bloc Party
96. I Don't Care - Fall Out Boy
97. Psycho - Puddle of Mudd
98. Oh My God - Mark Ronson ft. Lily Allen
99. The Pretender - Nirvana
100. Kids - MGMT