Cradle-Robbing Celebrities

After calling off the wedding in 2011, it seems 26-year-old Crystal Harris and infamous playboy Hugh Hefner are on their way to happily ever after: they tied the knot at the Playboy mansion on New Year's Eve. Hef had ended a relationship with 20-year-old twins to settle down with Harris, a December 2009 Playmate.

Image 1 of 62 Getty Images
    • heffwife.B.jpg
    • hefner_Shera Bechard.jpg
    • 117362283.jpg
    • hughhef.jpg
    • olsensplit.jpg
    • geffen-lingvall.jpg
    • dick-van-dyke-girlfriend.jpg
    • 0706_GeorgeElisabetta.jpg
    • jonas_ Goodrem.jpg
    • 070511 al pacino Lucila Sola.jpg
    • 070511 alec baldwin hilaria thomas.jpg
    • 115254157.jpg
    • jlodatingsmart1.jpg
    • taylorwood_johnson.jpg
    • jefflydiasplit.jpg
    • jeffkrissplit.jpg
    • jefftaniasplit.jpg
    • doug hutchinson.jpg
    • 114517379.jpg
    • lorenzo_lamas_050211.jpg
    • 1145131743.jpg
    • scar_penn_722.jpg
    • 121610RonWood01.jpg
    • 0727_linda_hogan.jpg
    • 081910SNL01.jpg
    • tom-cruise-katie-holmes.jpg
    • 043011 carey cannon.jpg
    • 0702PaquinMoyer.jpg
    • 11.27-megan-fox-disney.jpg
    • 0706MadonnaJesus.jpg
    • 0706perrybrand.jpg
    • 0702Marilyn.jpg
    • 0706matthewcamilla.jpg
    • logan2.jpg
    • 0702haydenp.jpg
    • 0706emmyrossum.jpg
    • evalongoria1.jpg
    • 0706melgibson.jpg
    • 0702KingSouthwick.jpg
    • judesienna.jpg
    • 0706DemiAshton2.jpg
    • ccarquette.jpg
    • kim1.jpg
    • murdoch1.jpg
    • 0706_AllenSoonYi.jpg
    • 082009-hookup-goldblum-raimonde.jpg
    • 0706_NickCage.jpg
    • 0706DouglasZeta1.jpg
    • 0706FlockhartFord.jpg
    • 0706AnistonMayer.jpg
    • 0706aubryberry.jpg
    • 0706sarandonrobbins.jpg
    • naveen.jpg
    • trump4.jpg
    • jameswoods.jpg
    • geena.jpg
    • olivanjohn.jpg
    • sheryl.jpg
    • ellen19.jpg
    • marytylermoore1.jpg
    • billy_joel_katie_lee.jpg
    • mick_jagger_scott.jpg
Replay Slideshow

Cradle-Robbing Celebrities

It seems like a necessary stop on the path of a Hollywood starlet: move to LA, go on auditions and date a man your father's age. Here are a few of our favorite celebrity couples who think age ain't nothing but a number.

Please wait. Your gallery will be ready in 5 seconds.

Leave Comments
Don't Miss

local

May 24, 2013

Remembering Victim of Drunken-Driving Crash

The family of a man killed in a drunken-driving crash last Memorial Day...

local

May 24, 2013

Group Honors Veterans' Final Resting Place

A Cleburne-based group has gathered 70,000 flags to place on the graves of veterans fo...

local

May 24, 2013

Hundreds of DISD Teachers to Be Fired

Hundreds of Dallas Independent School District teachers will be fired along with...

the-scene

May 24, 2013

Polka Festival Plays on in Tornado-Hit Ennis

Last week's tornado isn't keeping Ennis from