Skipper

This is one of my favorite jokes, but I have to warn you, it's a bit of a shaggy-dog joke.

So, there's a guy named Skipper who, at his work, is known for being a braggart and constantly making things up. Everyone in the workplace knows that Skipper's always telling ridiculous stories and they eventually learn to ignore it. Skipper's boss, though, can't stand it, and says to himself "this obnoxious kid is insufferable. I can't have him coming into the office everyday and spouting this bullshit, it's bad for productivity!" So he resolves that the next time Skipper starts bragging, he'll call him on his lies and put him in his place.

The next morning, as expected, he hears Skipper walking around the office saying "-no, really! I know EVERYONE in the world! Ask me about anybody, and they'll know who I am." People start gathering around Skipper, naming celebrities: "Kanye West" "Jennifer Lawrence" "Brad Pitt" "Yeah, guys," he answers, "I know all of them."

Interrupting, the boss walks in and says "Oh, so you REALLY know Brad Pitt? I don't believe you." "But I really do!" Skipper answers. "Then prove it to me!" his boss replies.

Skipper pulls out his phone and dials a number. Helistens for a couple seconds, then hangs up and says "Well, I guess he's not home, darn." His boss chuckles to himself, saying "Guess you don't know him after all! You better get back to work."

Skipper then says "How much do you want to bet? Since Brad and I are such good friends, he wouldn't mind me popping up at his house. Here's a bet: you buy plane tickets to LA for us. If you're right, and he doesn't know me, I'll pay you back double the price of the tickets."

His boss grins and says sure, and they head to the airport. On the flight, the boss asks Skipper, in a condescending tone, "So, how do you know Brad Pitt?" Skipper answers that they were actually college roommates. His boss rolls his eyes- there's no way this idiot was Brad Pitt's roommate!

They pull up to Brad Pitt's mansion and Skipper starts walking up to the lawn. "Hey, Skipper," his boss interrupts, "it's okay, you don't have to go on his lawn and get arrested or anything. Just pay me back for the tickets and we're all good." As he's speaking, though, Brad Pitt himself walks out in a robe and says "Hey, Skipper, my man! What's up! I slept in this morning and missed your call. My butler was just making me some breakfast- how would you and your friend like to stay and eat with me?"

They eat breakfast with Brad Pitt, and Skipper and he reminisce about their college antics. His boss, meanwhile, is steaming, and doesn't even enjoy the delicious breakfast.

As they leave, he says, "That was just a fluke! You got lucky. How about we go double or nothing, on someone else." "Sure," Skipper says, "but you'll be disappointed- I really do know everyone there is to know." "How about the president?" his boss proposes?

Skipper agrees. "Oh yeah, Barry and I had 5th period Biology together in High School! Good times." So, they fly out to DC.

When they get to the White House, Obama happens to be walking in the front door from his motorcade and spots Skipper across the lawn. "Hey, Skipper!" He shouts, "come over here!"

Skipper and the president do some sort of secret handshake and immediately begin talking like old friends, to his boss's disbelief. "I have a very busy schedule, as you might imagine, but I have a couple minutes right now if you wanted to grab coffee."

As Skipper and the president talk, Skipper's boss is even more upset. "I should be enjoying this. I met Brad Pitt and Obama today! But I just can't believe Skipper though, he's got to just be crazy lucky for me to pick the two famous people he knows," he thinks to himself.

So, as they leave, the boss makes one last bet with Skipper: "One more double or nothing. Anyone in the world, not just the country."

"I feel bad taking your money, boss! But, I'm having a great time today, so if you want to go see someone, I'll buy the tickets. And I ensure you, I'll know them." Skipper's boss cracks a smile and says "okay, we're on our way to the Vatican. Let's see the Pope!"

"Oh sure, I know him, boss!" Skipper replies excitedly. "I went to his church for a year before he became Pope."

They arrive at the Vatican just as the Pope is about to speak, and there's a massive crowd around the balcony. The Pope walks out and begins to address the crowd. The two Americans press as far as they can to the front of the crowd to get a good view, but they can only get about halfway in. Skipper tries to wave to him to get his attention, but there are far too many people.

"He'll never see me int he chaos here," Skipper remarks to his boss. "You know what? Since I know all of the guards, I'll just head up past them and meet him up on the balcony. You stay here and watch me come out."

Skipper runs into the building, saying hi to all of the guards on the way up. Once he's up there, he surprises the Pope. They have a nice conversation and Skipper waves to the crowd for a while with the Pope's hand on his shoulder before coming back down.

As he arrives back at where he and his boss were standing earlier, he sees an ambulance with a crowd of onlookers. To his surprise, his boss is on a stretcher in the back of the ambulance!

"Boss! Boss! Are you okay?" "Yeah, Skipper, I'm gonna be all right. I just fainted," his boss reassures him.

"Fainted? What happened?"

"Well," the boss replies, "I saw you come out onto the balcony and talk with the Pope. As you were waving to the crowd, another guy in the crowd turned to me and asked 'Hey, who's that-a guy on-a the balcony with-a Skipper?'"