We explore Rolling Stone's 250 Greatest Songs of the 21st Century
Kabous Le Roux
24 November 2025 | 10:31Dr Sheldon Leal, a musicologist at the Academy of Sound Engineering takes a journey through two decades of popular music.

Missy Elliott's 2001 hit ‘Get Your Freak On’ is the greatest song of this century, according to Rolling Stone.
The music landscape has transformed dramatically over the past 25 years, and Rolling Stone's latest list of the 250 Greatest Songs of the 21st Century attempts to capture this evolution. But can any list truly represent the fragmented, algorithm-driven musical world we now inhabit?
Leal shared his insights on the compilation, highlighting both its merits and limitations. "I always find these lists to be such a subjective thing," he remarked. "What is the metric that they're using to compile these lists? I think this is obviously the journalists who work at Rolling Stone trying to put something together that they feel represents what the 21st century looks like, and I think they have done quite a good job."
The list's top spot went to Missy Elliott's 2001 hit ‘Get Your Freak On’, a choice that reflects her pioneering influence. While Leal appreciates Elliott's contribution, he questions whether it truly deserves the number one position. "She is my favourite female rapper, so having Missy Elliott at number one makes me very happy. Do I think it is the most influential song of the 21st century? No, I do not.
What makes the list particularly interesting is how it captures the changing nature of music discovery and fame. Many artists featured achieved massive success through non-traditional channels like social media, sometimes bypassing mainstream recognition entirely. This fragmentation represents a significant shift from previous decades when ‘big hits’ dominated across platforms.
The top five selections heavily favour 2003, with Yeah Yeah Yeahs' ‘Maps’ at number two and The White Stripes' ‘Seven Nation Army’ at number four. About the latter, Dr Leal observed, "Every guitarist in the world wants to play that riff. I've heard that riff played to death like Stairway to Heaven. This is the 21st century's version of Stairway to Heaven."
Dr Leal also highlighted how streaming algorithms have changed our listening habits. "These algorithms are dictating to people what they will listen to," he explained.
"As a musicologist, I want to be able to listen across genres. So, I don't allow the algorithm to dictate to me because I'm very conscious of what I listen to." This algorithmiccuration has led to more insular listening experiences, with fewer opportunities for genre-crossing discoveries that were once common through music television and radio.
To hear more of Dr Leal's expert analysis on contemporary music trends and the full breakdown of this influential list, click below:
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