50 Best Wrestlers Of The 2020s (So Far)

18. Orange Cassidy

WWE Night Of Champions 2025 Cody Rhodes King Of The Ring
AEW

Like other AEW originals on this list, Orange Cassidy has become one of the most unique and beloved figures in professional wrestling during the 2020s primarily for serving to remind audiences why the challenger brand is so important. 

With his laid-back persona and unorthodox in-ring style, 'Freshly Squeezed' has served as a conscience and cornerstone of All Elite Wrestling - tags once assigned to The Undertaker at the peak of his powers in WWE. From 'Deadman' to deadpan, their drawn-in demeanours link them, as does the importance of suspension of disbelief in an era where most of the other old methods are done. Cassidy’s best matches blend comedy, surprising athleticism, and genuine emotion from a character that just exists on the fringes of reality. What seems like laziness at first quickly turns into Cassidy unleashing sharp counters and explosive offence, catching opponents and audiences alike off guard.

His character broke the mould of wrestling archetypes and inspired a wave of performers to embrace individuality and humour, as encouraged by AEW as a promotion. That it embraced him and others like him did as much for brand identity as a hundred cookie cutter matches. He’s proven that you don’t need to be loud and ostentatious to be unforgettable, and that despite what Justin Credible espoused in the late 1990s, it actually scans as pretty awesome when you can be the coolest and the best. 

Contributor
Contributor

Michael is a writer, editor, podcaster and presenter for WhatCulture Wrestling, and has been with the organisation over 8 years. He primarily produces written, audio and video content on WWE and AEW, but also provides knowledge and insights on all aspects of the wrestling industry thanks to a passion for it dating back over 35 years. As one third of "The Dadley Boyz" Michael has contributed to the huge rise in popularity of the WhatCulture Wrestling Podcast and its accompanying YouTube channel, earning it top spot in the UK's wrestling podcast charts with well over 62,000,000 total downloads. Within the podcasting space, he also co-hosts Benno & Hamflett, In Your House! and Podcast Horseman: The BoJack Horseman Podcast. He has been featured as a wrestling analyst for the Tampa Bay Times, Fightful, POST Wrestling, GRAPPL, GCP, Poisonrana and Sports Guys Talking Wrestling, and has covered milestone events in New York, Dallas, Las Vegas, Philadelphia, London and Cardiff. Michael's background in media stretches beyond wrestling coverage, with a degree in Journalism from the University Of Sunderland (2:1) and a series of published articles in sports, music and culture magazines The Crack, A Love Supreme and Pilot. When not offering his voice up for daily wrestling podcasts, he can be found losing it singing far too loud watching his favourite bands play live. Follow him on X/Twitter - @MichaelHamflett