10 Most Effective Wrestling Heels Of The 21st Century

5. CM Punk

Prince Devittt
WWE.com

CM Punk's holier than thou "Straight edge means I'm better than you schtick" was a revelation on the early 2000s; the act was so natural, unique and inherently loathsome that he was able to coexist as both super-worker and pure heel in an era in which the former automatically compromised the latter. Punk was at the forefront of the workrate revolution, contesting a classic trilogy with Samoa Joe in 2004, but his incendiary mic work and organic arrogance was so grating that he never found difficulty generating heat.

Punk's heel work was effective, in and of itself, but the buzz his unique act generated was such that it compelled WWE to sign a man they never would have otherwise considered. His look, his work, his attitude - WWE's influential tastemakers (Triple H and Shawn Michaels, most notably) hated everything about him - but he found major success eventually, largely as a result of his excellent 2009 series with Jeff Hardy in which he exhumed his old ROH act.

But Punk was no one-dimensional antagonist. His creepy, faux-messianic Straight Edge Society gimmick triggered conservative U.S. crowds - and after commanding a lasting level of universal respect upon his 2011 breakthrough, he still managed to perform as a heel throughout 2012 and 2013 with his cheap heat lark-about work with Paul Heyman.

Punk, gone for three years, remains a heel to many who have chastised him for departing wrestling so abruptly and denouncing it as fake on the way out.

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Michael Sidgwick is an editor, writer and podcaster for WhatCulture Wrestling. With over seven years of experience in wrestling analysis, Michael was published in the influential institution that was Power Slam magazine, and specialises in providing insights into All Elite Wrestling - so much so that he wrote a book about the subject. You can order Becoming All Elite: The Rise Of AEW on Amazon. Possessing a deep knowledge also of WWE, WCW, ECW and New Japan Pro Wrestling, Michael’s work has been publicly praised by former AEW World Champions Kenny Omega and MJF, and current Undisputed WWE Champion Cody Rhodes. When he isn’t putting your finger on why things are the way they are in the endlessly fascinating world of professional wrestling, Michael wraps his own around a hand grinder to explore the world of specialty coffee. Follow Michael on X (formerly known as Twitter) @MSidgwick for more!