WOW, that was some good irony.

I was watching the Seinfeld episode “The Masseuse” the other night. There’s a subplot where Elaine is dating a guy named Joel Rifkin - the same name as a serial killer. He’s upset about this after being paged at a Giants game, and decides to change his name to avoid the embarrassment of being confused with a murderer. He and Elaine start talking about potential names while she’s reading Sports Illustrated, and she suggests. . . OJ.

At first, I thought that it was a joke thrown in by the writers, until I looked it up and saw that the episode aired several months before the murders! I don’t want to get into a discussion about the fact that OJ was acquitted, I just want to discuss good examples or real-life irony.

Any good observations?

I’m not sure it counts as irony, but there was one episode of the Burns and Allen radio show where Gracie is trying to get George to take an experimental drug that will allow him to live to 100. George Burns actually went on to live until shortly after his 100th birthday.

Another good example is an old Saturday Night Live episode that featured a short with John Belushi as an old man walking through the cemetery and commenting on his deceased SNL castmates and how they died. Very spooky to watch now.

Yup. And not only that, but he has a line where he says, “Yeah, they all thought I’d be the first one to go.” : SNL Transcripts: Art Garfunkel: 03/11/78: Schiller's Reel: Don't Look Back In Anger - SNL Transcripts Tonight

::shudder::

There is the line in Monkey Business where Groucho says to Thelma Todd, “You look like a girl who had a lot of bad breaks. I could clean and tighten those brakes, but you’d have to stay in a garage overnight.”

A few years later, Todd was dead under mysterious circumstances. She was found in her garage, killed by carbon monoxide poisoning. She had been there overnight.

One of the Ironic Moments that has to be high on the list is James Dean’s TV spot advocating auto safety:

It’s tragic, and perhaps “too soon”, but Daniel von Bargen played the Commandant Spangler, head of the military academy in Malcolm in the Middle, and had lost limbs, and an eye, but not due to any wartime combat.

A few days ago, he botched a suicide attempt, shooting himself in the temple (most likely losing an eye, maybe both), because diabetes had taken one of his legs, and he was about to go in to get some toes amputated from his other foot.

And to add another layer, tying back into the OP, he played George’s apathetic boss Kruger on Seinfeld.

Where’s the Human Fund when you need it?

In his novel Why Not Me?, Al Franken writes a fictional account of his 2000 Presidential run. In the book, Franken chooses Joe Lieberman as his running mate (the joke being that Franken chooses an all-Jewish administration).

Why Not Me? was published in January 1999. A year and a half later, Lieberman would be chosen as the genuine Democratic Vice Presidential nominee for the 2000 election.

I think that’s coincidence, not irony.

Perhaps, but it was written in the sense that Joe Lieberman being Vice President was as unbelievable as Al Franken being President.

Of course, now that Franken is no longer in show business and has been elected to the Senate, the humor of the idea of him running for President has also diminished.

Stan Freberg did a recording in 1966 satirizing Ronald Reagan’s run for governor. It ended with a reference to him aspiring to the Oval Office.

(While searching for a little background, I found a thread from just last fall: Weird Coincidences Between Fiction and Real Life.)

Mad Magazine ran this ad on the back cover of issue #131 (Dec. 1969):

Not really irony, but too good not to mention: about 20 years before the OJ trial, the O’Jays had a top ten hit called “Back Stabbers.”

And their follow-up single was “992 Arguments”. Prescient, what!

In “Demolition Man” there’s a scene where Wesley Snipes is freeing a bunch of cryogenically frozen criminals. One of the names on the convict list he’s looking at: Scott Peterson.

The movie was released in 1993, nine years before Lacey Peterson was murdered.

Action Comics #1, dated June 1938, had a guy denying that he killed “Jack Kennedy.”

Fredric Brown’s first novel, The Fabulous Clipjoint, features a crook named “Dutch” Reagan.

I don’t think this is really ironic; it’s just sad. The joke in the sketch is that everybody thought Belushi was going to die young because of all the drugs he was doing - to the point where they could make a joke out of it in a sketch and everybody got it. Meanwhile he actually did die young from drugs like people thought he might, unfortunately. The bit about Gilda Radner is even sadder.

Being evil, I’m simply going to present these links:

Funny Aneurysm Moment
Harsher in Hindsight

I believe you will find ample fodder there. Notably, both contain the Belushi bit.

Yeah, but Dean actually had the right-of-way. Turnipseed was at fault.