9
World's Longest limousine

The longest limousine in the world is a true testament to making things bigger than everyone else, and if that means utterly destroying the original function then by God, we'll do it because this is America, son, and your Commie notions of "efficiency" and "not pissing resources down the vast hole of ego" won't fly here. Over 30 meters long with 12 sets of wheels, this abortion of internal combustion has one function only--to make its owner feel like a real man:

As you can see, it has its work cut out. There is not a single element of this picture that is not tragically failed overcompensation. Even the panther looks embarrassed to be near him, and that's a fucking cat wearing a necklace.
If Limo Bob was spending any more on compensation, he'd be Paul McCartney. The limo claims to have a helipad and a swimming pool (complete with diving board), but considering that the only person to land a helicopter on a moving car was Howlin' Mad Murdock (retired) and that the car is still only the width of a regularly-stupid limo, what you really have is a square of roof and a bath that someone's nailed a plank over. And most cars have roofs already.
We must admit that technically, this car almost succeeds, in that it will make people say, "Wow, whoever owns that is a huge dick."
8
The Jeddah Mile High Tower

Prince al-Walid bin Talal has told the world in no uncertain terms "Mine is bigger than yours." And when the world asked, "Our what?," he replied "Whatever, it doesn't matter. I'm building a tower a goddamn mile high."
This tower is specifically designed to kick the hell out of the still-in-progress half-mile-tall Burj Dubai tower, a country that has itself pretty much quit its day job to build ridiculous engineering projects full time. We suppose that's what happens when a country has a million men of median age 27, a $37 billion dollar GNP and only 300,000 women.

That's a difficult enough group dynamic for a free love commune, never mind an Islamic nation. The only reason the entire country of Dubai hasn't simply burned down is because they channel their frustrations into things like the largest man-made harbor in the world, the largest indoor ski resort in the world, until they finally said "Fuck it, let's just build a giant cock."
That got the attention of Talal, the Saudi billionaire who knew he couldn't stand idly by. Thus he proposed his $10 billion, mile-high project bringing him one step closer to his dream to make a building that could fuck the moon.