1. Arnold Schwarzenegger is Drake: A foreign-born former actor who seemed like an impossibility only to do a shockingly good job.
2. Richard Nixon is Rick Ross: Presently a joke but, if we’re being honest, provided us with way more entertainment than we thought.
3. Rand Paul is Tyler the Creator: A little bit crazy, occasionally dead on, but you’re embarrassed to be caught vibing to him.
4. Grover Cleveland is Birdman: The two of them were good personal friends, and Cleveland saw Birdman as a father figure of sorts.
5. Barack Obama is Wale: He’s great, I guess? Most people focus on the latter half, and the hanging question-mark of disappointment.
6. Elizabeth Warren: Is A$AP Ferg- I’m sure she’s great, fine, whatever, but I’m not that deep into rap to give more than a cursory look.
7. George Washington is Biggie: Just the best, classic, constantly enjoyable.
8. Tupac Is Lincoln: More politically significant than Washington, more challenging work, but Washington’s greatness was equally thorough
9. Bobby Kennedy is Big L: potentially the greatest, lionized most by the most knowledgable, and cut down even before their prime.
10. John Edwards is Chris Brown: A repulsive twerp who made us swoon, like, eight years ago.
11. Bill Clinton is Andre 3000: A great who is even more popular while doing almost nothing.
12. Hillary Clinton is Big Boi: The other half of Andre 3000, arguably better, obviously harder working and more solid albeit less charming
13. Howard Dean is Meek Mill: A solid all-around guy undone by our focus on his yelling.
14. Ralph Nader is Papoose: Absolutely dedicated to to being authentic to their ideals, which is a trait that fucks up everything they do.
15. Reagan is Big Pun: Good, but a weird, obligatory add-on to “all time best” lists not nearly as good as the other “all time bests.”
16. Herman Cain is Wacka Flocka Flame: Quite entertaining and enjoyable, surprisingly affable, but also kind of a self-aware joke.
17. George W. Bush is Vanilla Ice: Loathed at the time, always mocked, but softened over time through nostalgia.
18. Dick Cheney is Suge Knight: The diabolical comic-book-style villain pulling the strings behind Vanilla Ice, others.
19. John McCain is Lil Wayne: Formerly a deeply respected, potential president, now more of a relic of a bygone era. Both enhanced by cough syrup (required/ recreational)
20. Al Gore is Lupe Fiasco: We liked him even though he was preachy and he didn’t quite win. Now we’re bored of him even if he’s kind of obviously right.
21. Joe Biden is Ludacris: He’s fun, funny, veteran but shockingly capable and talented when it comes right down to it.
22. Nancy Pelosi is 50 Cent: Hate on haters. Even when you forget about them, their history is still unforgettable. Also, way richer than you thought.
23. Chris Christie is Action Bronson: Good at what he does, but that doesn’t make him likable per se.
24. Paul Ryan is Mac Miller: Kind of bro-y, honestly, not the worst, but the problem is he’s loved most by the people who are the worst.
25. Bill De Blasio is Kendrick Lamar: Everyone is eager to love him as the next big thing, and sure, he’s great, but let the man breathe, you know?
26. Aaron Burr is Chief Keef: Kind of a footnote, but got our attention as we rubbernecked the historical violence.
27. Ted Kennedy is Jay-Z: A rich, powerful east-coat icon, who, while great, mostly just outlived the other contemporary greats of his era while banking on their history.
28. Ulysses S. Grant is Bun B: Fantastic, southern, kind of forgotten in the shuffle of other, flashier president/rappers.
29: Warren G. Harding is Warren G: Both were rocked by the Teapot Dome scandal of 1923.