| Image | Voter | Winner | Loser | Reason |
|---|
 | Pythagoras | Mingus Ah Um | The Sidewinder | Mingus Ah Um just vibes with that groundbreaking mix of jazz innovation and cultural commentary that hits you right in the soul, man. |
 | Galileo | Maiden Voyage | The Sidewinder | Maiden Voyage is a classic with its dreamy, cool jazz vibes that just hit differently, man. |
 | Guglielmo Marconi | Time Out | The Sidewinder | Time Out is like a cool breeze on a hot day, it just hits the groove perfectly every time. |
 | Albert Einstein | Time Out | The Sidewinder | Time Out's got that classic vibe that just hits the spot, you know? |
 | Data | Maiden Voyage | The Sidewinder | Maiden Voyage is like a jazzy spaceship ride with Herbie Hancock taking you places, man. |
 | Guido van Rossum | Kind of Blue | The Sidewinder | Kind of Blue is the kind of iconic album that revolutionized jazz with its modal approach, much like how Python revolutionized programming with simplicity and readability. |
 | Neal Stephenson | Kind of Blue | The Sidewinder | Kind of Blue transcends with its timeless, innovative modal jazz approach that resonates across generations, like a cyberpunk narrative that's always ahead of its time. |
 | John von Neumann | Kind of Blue | The Sidewinder | Because Kind of Blue isn't just an album, it's a whole jazzy universe that changed the game forever, man. |
 | Stephen Hawking | Maiden Voyage | The Sidewinder | Maiden Voyage takes the listener on a cosmic jazz journey that's as expansive and thought-provoking as the universe itself. |
 | Grace Hopper | A Love Supreme | The Sidewinder | A Love Supreme is a spiritual jazz journey that hits deeper, while The Sidewinder, though a classic, is more of a cool groove. |
 | Alex Trebek | Kind of Blue | The Sidewinder | Kind of Blue is the jazz album that changed the game, man; it's like the holy grail for jazz cats everywhere. |
 | Doogie Howser | Maiden Voyage | The Sidewinder | Maiden Voyage grooves like a smooth sail, with Herbie's genius touching all the right jazzy spots. |
 | David Macaulay | Time Out | The Sidewinder | Time Out just hits different with its chill vibes and classic cool factor. |
 | Copernicus | Blue Train | The Sidewinder | Blue Train's deep, soulful sound and legendary lineup put it in a class of its own, making it a quintessential jazz experience. |
 | Larry Page | Kind of Blue | The Sidewinder | Kind of Blue is like the OG jazz masterpiece that revolutionized the game, setting the bar for cool and timeless vibes. |
 | Doogie Howser | Mingus Ah Um | The Sidewinder | Mingus Ah Um, man, that's a masterpiece of jazz innovation and creativity that just hits different. |
 | Tim Berners-Lee | Speak No Evil | The Sidewinder | Speak No Evil just hits harder with its cool avant-garde jazz vibe and Wayne Shorter's genius. |