On New Year’s Eve, Playboy founder and extremely old person Hugh Hefner married his on-again/off-again fiancée — and, surprise!, December 2009 Playmate of the Month — Crystal Harris. The bride wore a lovely pink Romona Keveza gown and the groom wore a diaper: Mr. Hefner is 86, his new bride is 26. That’s right, their age difference is greater than the life expectancy rate in Cambodia (59.7).

All jokes aside, I wish them much happiness. Love springs eternal, particularly between the very old and rich, and the very young and blonde. Hef’s desire to get married for the third time is impressive considering that a few years ago he was happily cavorting with his own harem of live-in girlfriends and that, following their last breakup, Harris said some fairly unflattering (and wholly unsurprising) things about the man’s stamina in bed. Hef must be very forgiving. Or just forgetful.

Let’s take a look at three other May-December celebrity marriages and see how things bode for Mr. and Mrs. Hefner.

Clint Eastwood and Dina Ruiz
After being married and divorced once, carrying on a long-term and tumultuous relationship with married actress Sondra Locke and fathering six children by four different women, Hollywood legend and noted chair-insulter Clint Eastwood was looking to settle down. He married news anchor Dina Ruiz, 35 years his junior, in 1996.

How it bodes for the Hefs: QUITE WELL. These two crazy kids are still together after 16 years. Mind you, Clint’s wife and daughter star together in a nightmarish reality show, but Hef should be used to that kind of thing by now.

Anna Nicole Smith and J. Howard Marshall
It was a match made in Heaven — wait, sorry, I meant to say “Pleasures,” a Houston-area strip club where Anna Nicole Smith and oil tycoon J. Howard Marshall met in 1991 while she was performing and he was, just a guess, drooling. Anna was a top-heavy 24-year old dancer and J-Ho (heh) was a smitten 87-year old billionaire. They wed in 1994, with Smith claiming the 63-year age difference didn’t bother her.

How it bodes for the Hefs: NOT WELL. Marshall died thirteen months later, presumably from his eyes popping out of his head, cartoon wolf–style. Almost immediately, the legal wrangling started over his $1.6 billion fortune. It went to the U.S. Supreme Court twice, with rulings going two different ways. The case outlived Smith herself, who died in 2007.

Zsa Zsa Gabor and Frédéric Prinz von Anhalt
Whoo boy! In 1986, Gabor married for the ninth time, to socialite, masseur and strangest person in the world Frédéric Prinz von Anhalt. Twenty-six years Gabor’s junior, von Anhalt was previously adopted as a 36-year-old man by the daughter-in-law of German Emperor Wilhelm II. It seems the apple doesn’t fall far from the, well, surrogate tree, because as a couple, Gabor and von Anhalt have themselves adopted ‘several’ adult men. In addition to “Adult Adoptions,” von Anhalt’s Wikipedia page contains such headings as “Robbery and Stripping,” “Bid for Governor of California” and “Accident Prone”; that last one describes the time Fréddie swallowed a bee and the time he glued his eye shut with nail glue. Oh, he also claims to have a decade-long affair with none other than Anna Nicole Smith.

How it bodes for the Hefs: IT DEPENDS. One one hand, these two are still married after 26 years, which is particularly impressive when you consider that Gabor was once married for a single day. On the other hand, von Anhalt has been accused of isolating Gabor from her family, and there have been numerous bitter legal battles over her care as her health has deteriorated. He also claims he wants to plastinate her body after she dies, and that she has expressed interest becoming a mother at age 94. In 2011, von Anhalt threw a lavish 25th anniversary party (well, as lavish as any party that had Frank Stallone as a guest can be) that did not feature his wife. Hmmmm…

Why do we encourage, and take giddy pleasure in, the May-December marriages of celebrities? Someone, please explain in the comments!

Paul BeerPaul Beer is a Toronto writer, actor and comedian. You can follow him on Twitter @pauldanielbeer.