1. Grease is the word?
Ron Galella, Ltd. / WireImage
June 1988
2. Tendril Attack!
Time Life Pictures / DMI / The LIFE Picture Collection / Getty Images
January 1991
3. Full-on Tarzan
Barry King / WireImage
November 1994
4. Waved Out
Jeff Haynes / AFP / Getty Images
January 1996
5. The "I'm dating Gwyneth Paltrow."
Kevin Mazur / WireImage
March 1997
6. Piecey Platinum
Getty Images
January 1998
7. "Is this how you use gel?"
Ron Galella, Ltd. / WireImage
April 1998
8. Buzzed
Andrew Shawaf / Getty Images
February 1999
9. Borderline Mullet
Ron Galella, Ltd. / WireImage
September 1999
10. The Ellen DeGeneres
Hugo Philpott / AFP / Getty Images
August 2000
11. The Keith Urban, Circa 2000
Steve Granitz / WireImage
January 2002
12. Castaway Chic
Jon Kopaloff / WireImage
August 2002
13. Are those extensions?
Steve Granitz / WireImage
April 2003
14. Back to Buzz
Stephen Lovekin / FilmMagic
May 2004
15. The Billy Idol
L. Cohen / WireImage
June 2005
16. The Frat House Special
Evan Agostini / Getty Images
September 2006
17. The Frat House Special, Highlights Edition
Amy Graves / WireImage for BWR Public Relations
January 2007
18. Classic.
Anne-Christine Poujoulat / AFP / Getty Images
May 2007
19. That haircut every boy had in the mid-2000s.
Steve Granitz / WireImage
June 2007
20. Are those blond tips?
James Devaney / WireImage
September 2007
21. Pretend Rockstar
Jon Kopaloff / FilmMagic
January 2008
22. "I just got out of the shower."
Pascal Le Segretain / Getty Images
August 2008
23. "I'm a dad now."
Jeff Vespa / WireImage
January 2009
24. "But a cool dad."
Barry King / FilmMagic
August 2009
25. Feathered Fringe
Jean Baptiste Lacroix / WireImage
July 2010
26. Here we go again.
Pascal Le Segretain / Getty Images
November 2010
27. Growing it out.
Ian Gavan / Getty Images
May 2011
28. Oh wow.
Jun Sato / WireImage
November 2011
29. "Cut your hair." - Brad Pitt's mom, probably.
Caroline McCredie / Getty Images for Paramount Pictures
June 2013
30. "OK, mom. Geez." - Brad Pitt, probably.
Steve Granitz / Getty Images
January 2014
31. Fresh at 50
Han Myung-Gu / WireImage
November 2014
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