Is it Ironic?

That one song comes up a lot as an example of the misuse of the word. Is it ironic? It could be with more context. Some of the lines need more context than others in order to qualify as ironic. I can't believe I'm about to do this when this lame song has been around for so long, but here goes. 

"An old man turned ninety-eight / He won the lottery and died the next day"

Yes, if he was struggling his whole life, no if not. In this case ‘turning 98’ is redundant to ‘died the next day’ - the point could be made equally since 98 year old people aren't really able to enjoy most things money can buy and it's a given that death is in the mail.

"It's a black fly in your Chardonnay"

Maybe with some convoluted context like it’s an exterminator celebrating a promotion to head exterminator or something.

"It's a death row pardon two minutes too late"

Maybe if the accused was known as the Punctual Killer or something like that.

"It's like rain on your weddin' day"

No, unless you’re experiencing a drought and decide at least you can get married without it getting rained out.

"It's a free ride when you've already paid"

Not by itself, though it’s primed for irony. You’d just need the extra detail like going out of your way to get payment for the ride (figuratively or literally).

It's the good advice that you just didn't take

By no means.

"Mr. Play It Safe was afraid to fly / He packed his suitcase and kissed his kids goodbye / He waited his whole damn life to take that flight / And as the plane crashed down he thought"

Sure. He didn’t fly all those years, all those planes probably didn’t crash. He finally does and it crashes. Irony.

"Well life has a funny way of sneakin' up on you / When you think everything's okay and everything's goin' right, right / And life has a funny way nobody helpin' you out when / You think everyhing's gone wrong and everything blows up in your face"

The key here is that it’s not ironic if everything is going a certain way and then there’s a 180 of fortune, it’s only ironic if you have every reason to believe that it will go a certain way and it goes the opposite way.

"A traffic jam when you're already late"

Nope.

"A no smoking sign on your cigarette break"

There’s enough suggested here to give this one to her. Like this well-earned break is symbolized by a cigarette you're allowed to take by those in authority, only to find some other authority disallowed it.

"It's like ten thousand spoons when all you need is a knife"

Not unless you threw away your knife in order to get all them spoons.

"It's meetin' the man of my dreams / And then meetin' his beautiful wife"

Convoluted context required again. I.e. ok if the wife turns out to be the person who convinced you to leave someone else because the man of dreams was so great.