In a perfect world, wrestlers would turn from heel to face, or vice versa, only once or twice in their career. Actually, in a perfect world, they'd all be babyfaces and no one would ever resort to violence, but said perfect world would absolutely suck.
To my original point, you really don't want wrestlers changing allegiances as often as they change their underwear (TNA - please take note! Also, don't get caught up in the underwear part; it's just an analogy). It means so much more when fans are wondering "Why did Mr. X turn heel? Why did Mr. X turn face? Why would a wrestling promotion invest so much time in Mr. X?" etc.
With that preamble out of the way, I've taken a look at ten wrestlers that have shifted sides more than their fair share. In fact, unless my math and memory skills suck, these should be the ten folks that have turned the most among the major companies of WWE/WWF, WCW, TNA, ECW and AWA.
A couple of factors that were part of my analysis: if a wrestler was a heel/face for one night only or teased turning but ultimately didn't, it doesn't count. However, if they jump from promotion to promotion while making the switch, that works. Same with wrestlers switching allegiances while still being a heel or face, so long as its pretty definitive (only a few examples of this, but you'll see it pop up once or twice).
Ready? Let's examine some chronic turncoats!
Lex Luger
The Total Package needed 11 turns to be complete.
Year
Promotion
Details
1988
NWA
Turned face after being kicked out of The Four Horsemen.
1989
NWA
Turned heel following a match against Michael Hayes.
1990
NWA
Turned face by supporting Sting.
1991
WCW
Turned heel by aliging himself with Harley Race.
1993
WWF
Turned face by bodyslamming Yokozuna.
1995
WCW
Turned heel by attacking Hulk Hogan and aliging himself with Jimmy Hart.
1996
WCW
Turned face after being attacked by Ric Flair.
1999
WCW
Turned heel by attacking Bill Goldberg and joining the united nWo Hollywood and Wolfpac.
2000
WCW
Turned face as part of the Millionaires Club.
2000
WCW
Returned as a heel tag team with Buff Bagwell.
2006
TNA
Returned as an ally of Sting, after previously being booked as a heel.
Kurt Angle
Nine turns in eleven years? What's Angle been drinking (ooh, don't answer that)?
Year
Promotion
Details
1999
WWF
Turned heel after previously appearing on Sunday Night Heat and dark matches as an All-American.
2001
WWF
Became face as part of InVasion angle.
2001
WWF
Turned heel after aligning with Vince McMahon at the conclusion of the InVasion angle.
2003
WWE
Returned as a face after coming back from neck surgery.
2004
WWE
Turned heel against Eddie Guerrero.
2006
WWE
Became a face after winning the World Heavyweight Title in a battle royale.
2007
TNA
Turned heel against Sting.
2009
TNA
Turned face by putting over Matt Morgan.
2011
TNA
Turned heel by aligning with Hulk Hogan.
The Big Show
With an amazing 16 turns (so far), Show appears to be The World's Largest Turncoat.
Year
Promotion
Details
1996
WCW
Went from Dungeon of Doom to nWo, effectively turning his back on WCW.
1996
WCW
Became face after being kicked out of the nWo.
1998
WCW
Rejoined the nWo.
1999
WWF
Quit The Corporation after attacking Vince McMahon.
1999
WWF
Turned heel as part of a tag team with The Undertaker.
1999
WWF
Turned face during a feud with The Big Boss Man.
2000
WWF
Turned heel following a confrontation with The Rock.
2000
WWF
Became a face in the wake of his comedic Saturday Night Live cameo.
2000
WWF
Became a heel as part of a faction with Shane McMahon, Chris Benoit, Kurt Angle, Edge and Christian.
2001
WWF
Was turned into a face as part of the InVasion angle.
2002
WWE
Turned heel against Steve Austin and aligned himself with Ric Flair.
2004
WWE
Returned to SmackDown as a face, feuding with Kurt Angle.
2006
WWE
Became a heel by turning on Raw and joining ECW.
2008
WWE
Morphed into a face during his feud with Floyd "Money" Mayweather.
2009
WWE
Turned heel by aligning himself with Vickie Guerrero.
2010
WWE
Turned face against The Miz.
Christian
Still has a lot of peeps for someone who has turned 10 times.
Year
Promotion
Details
1999
WWF
Turned face when he and Edge parted ways with Gangrel.
2000
WWF
Turned heel with Edge during a feud with The Hardy Boyz and The Dudley Boyz
2001
WWF
Along with Edge, became a face during the InVasion angle.
2001
WWF
Turned on Edge.
2002
WWF
Became a protege of Diamond Dallas Page.
2002
WWF
Turned on Diamond Dallas Page.
2005
TNA
Debuted as a face.
2006
TNA
Turned heel on Sting.
2008
TNA
Became a face after Kurt Angle and The Christian Coalition turned against him.
2011
WWE
Turned heel following a match with Randy Orton.
Kane
15 turns, most of them involving the same friggin' guy.
Year
Promotion
Details
1997
WWF
Briefly sided with The Undertaker as a face, despite Paul Bearer's wishes.
1998
WWF
Turned heel on The Undertaker.
1998
WWF
Turned on by The Undertaker and Paul Bearer, becoming a face.
1999
WWF
Joined The Corporation as a heel, against his free will.
1999
WWF
Kicked out of The Corporation, and became part of a face team with X-Pac.
2000
WWF
Turned heel on The Undertaker.
2001
WWF
Joined forces with The Undertaker, becoming a face.
2003
WWE
Turned heel on Rob Van Dam after being forced to unmask.
2004
WWE
Became a face during feud with Snitsky.
2006
WWE
Turned heel against The Big Show because of "May 19" voices in his head.
2006
WWE
Turned face after defeating Impostor Kane.
2008
WWE
Turned heel as part of a feud with Rey Mysterio.
2009
WWE
Became a face after saving The Undertaker.
2010
WWE
Turned heel after it was discovered he'd put The Undertaker in a "vegetative state."
2011
WWE
Became part of a face tag team with The Big Show.
Vince McMahon
Don't Cross The Boss, unless you want him turning on you 13 times.
Year
Promotion
Details
1998
WWF
Transformed from multicolored suit-wearing face announcer to evil owner during feud with Stone Cold Steve Austin.
1999
WWF
Turned face during a feud with The Undertaker and The Corporate Ministry.
1999
WWF
Became a heel when it was revealed he was "The Higher Power".
1999
WWF
Turned face during a feud with Triple H.
2000
WWF
Turned heel on The Rock and reunited with his children.
2001
WWF
Became a de facto face during the InVasion angle.
2001
WWF
Turned heel the night after the InVasion angle ended.
2005
WWE
Became a face during his mini-feud with Raw GM Eric Bischoff.
2006
WWE
Returned to his evil owner gimmick for a feud with Shawn Michaels.
2008
WWE
Became a face when he introduced McMahon's Million Dollar Mania.
2010
WWE
Turned heel during a storyline with Bret Hart.
2010
WWE
Was turned face after The Nexus attacked him.
2011
WWE
Appeared as a heel while suspending CM Punk.
Ric Flair
16-time World Champion. 14-time Turncoat. Woooooo!
Year
Promotion
Details
1983
NWA
Turned face during feud with Harley Race.
1984
NWA
Turned heel en route to forming The Four Horsemen.
1989
NWA
Turned face after being attacked by Terry Funk.
1990
NWA
Turned heel after The Four Horsemen attacked Sting.
1993
WCW
Returned to promotion as a face, feuding with The Hollywood Blondes.
1994
WCW
Turned heel during a match with Rick Steamboat to accomodate the debut of Hulk Hogan.
1996
WCW
Turned face as part of the WCW vs. nWo angle.
1999
WCW
Turned heel during a match with Hulk Hogan.
2000
WCW
Turned face during feud with Shane Douglas.
2000
WCW
Turned heel as leader of The Magnificent Seven.
2001
WWE
Returned to the promotion as a face co-owner.
2002
WWE
Turned heel on Stone Cold Steve Austin.
2004
WWE
Turned face during a match with Kurt Angle.
2010
TNA
Debuted in promotion as a heel manager for AJ Styles.
AJ Styles
10 turns over nine years, in the same promotion? Not Phenomenal.
Year
Promotion
Details
2002
TNA
Turned heel against Jerry Lynn.
2003
TNA
Became face after a confrontation with Vince Russo.
2003
TNA
Became a heel after aligning himself with Vince Russo.
2003
TNA
Turned face as Jeff Jarrett became a heel.
2006
TNA
Turned heel on Christopher Daniels and Rhino.
2007
TNA
Became a tweener, along with Tyson Tomko.
2007
TNA
Turned on Christian and sided with Kurt Angle, becoming a heel.
2008
TNA
Became a face during a feud with Kurt Angle.
2010
TNA
Aligned himself with Ric Flair and became a heel.
2011
TNA
Became a face, along with the members of Fortune, in a feud with Immortal.
Mick Foley
11 turns for The Hardcore Legend, or roughly 3 1/2 per personality.
Year
Promotion
Details
1992
WCW
Became a face during feud with Harley Race and Paul Orndoff.
1994
WCW
Turned heel on Kevin and Evad Sullivan.
1994
ECW
Debuted as a face.
1994
ECW
Turned on Tommy Dreamer.
1997
WWF
Turned face during a series of sit-down interviews ith Jim Ross.
1998
WWF
As "Dude Love", turned heel against Stone Cold Steve Austin.
1998
WWF
Turned face following an attack by Kane.
2005
WWE
Aligned himself with Edge against the ECW faction.
2006
WWE
Turned face after saving Melina from Mr. McMahon
2009
TNA
Turned heel after attacking Abyss.
2009
TNA
Saved Abyss from Dr. Stevie and became a face.
Kevin Nash
TWENTY turns for Big Sexy? Not including the numerous one-day "turns" he pulled off in WCW? No wonder CM Punk doesn't trust him!
Year
Promotion
Details
1994
WWF
Turned face on Shawn Michaels.
1995
WWF
Turned heel during match against Bret Hart.
1998
WCW
Turned face by leaving nWo and forming nWo Wolfpac.
1999
WCW
Turned heel by uniting nWo Wolfpac and Hollywood factions.
1999
WCW
Became a face during a feud with Sid Vicious and Randy Savage.
1999
WCW
Turned heel on Hulk Hogan.
2000
WCW
Was betrayed by heel faction The Natural Born Thrillaz, making him a face.
2002
WWF
Returned to promotion as part of heel nWo stable with Hulk Hogan and Scott Hall.
2003
WWE
Returned to promotion as face, feuding with Triple H.
2004
TNA
Debuted in promotion as heel as part of the Kings of Wrestling stable.
2005
TNA
Turned face in feud with Jeff Jarrett.
2006
TNA
Returned to promotion as heel X-Division-killer character.
2007
TNA
Turned face during conflict with Kurt Angle.
2008
TNA
Turned heel on Samoa Joe.
2009
TNA
Became a face, feuding with Eric Young and The World Elite.
2009
TNA
Aligned with The British Invasion and turned heel.
2010
TNA
Was turned on by Band members Syxx-Pac and Scott Hall.
2010
TNA
Turned on Eric Young and sided with Syxx-Pac and Scott Hall.
2010
TNA
Became a face during the Immortal angle.
2011
WWE
After debuting earlier in the year as a face, attacked CM Punk at SummerSlam and became a heel.