High Flyer Pillows

Pilot with champagne.

'You need a bigger pole.'

"I've been rich and I've been super-rich. Super-rich is better."

'Wow! That's got to be some sort of record!'

Skydive

Too late, Andy discovers that Red Bull doesn't, in fact, give you wings.

Missing you.

Sky Diver Losing His Wallet.

Pole vault crossing.

"This is my first jump!"

'The stock market closed early today due to an outbreak of 'altitude sickness'.'

"Pssst! Here's your cup of W-A-T-E-R."

'Could you throw me the car keys?'

'Shall I box up the shoes, or does your son want to fly them home?'

'Come on! You only live once!'

'The bar's gone up to six foot six.'

Private Jet

Man flying above the clouds

"Everything is outsourced. All that is left is to resign and receive my golden parachute."

A bear flying a plane upside down, waving to a man in another plane.

'Hi, I'm a sky marshall, you?'

Flying carpets.

Graduating Skydiving Academy.

Extreme Skydiving

An airplane is about to fly into a monster's mouth

'Where does he think he is - Wall Street?'

'Let's just say he's heightened his expectations.'

Trapeze artists.

I ran halfway across before I realized it wasn't a (cursing symbols) telephone wire.

Parachuting

The only thing I have to offer is my own confusion."

"How the hell do I afford to do this?"

"O.K., Mr. Spinelli, you're up. Now bank her to the right, and I'll talk you back in for a nice smooth landing."

"We'll begin boarding our first-class passengers after a ten-minute pause in honor of the even wealthier people who fly in private jets."

"We are now boarding priority travellers. Please be ready to present an air of entitlement."