Disclaimer: All things SPN belong to Eric Kripke, et al.

One – Telemarketer

While Sam was off researching the history of the building that housed the telemarketing company, Dean had charmed his way into a job in order to get a look around the place. After a few hours, the mindless repetition was starting to drive him nuts. Seriously, who buys these magazines, he wondered. Dean had just about decided it was time to bolt, and maybe come back later when Sam had more info. However, when the next call was answered by the sexiest voice this side of porn, Dean decided to stick around.

Six hours later the floor manager was escorting Dean off the premises with a look of disgust on his face. Dean didn't care. He'd gotten that girl from Alabama off, he'd secured certain promises from a coed at UNC Chapel Hill and, best of all, he'd found out exactly whose remains needed to be burned in the Meadowville Cemetery. All in all, he thought he had made a hell of a telemarketer.

Two - Sandwich Shop

"How come I have to take the shitty jobs while you sit in the nice air conditioned library?" Dean groused as he exited the Impala.

"Are we really going to have this conversation again?" Sam said as he maneuvered himself across the front seat and behind the wheel.

Dean leaned into the window to glare. 'Yes we do,' he said with a look. But as he began their staring contest, he could tell from the determined look on Sam's face that he would lose. They finished their silent conversation with Dean backing away from the car and Sam confirming with a raised palm that he would be back at five o'clock.

Dean headed into the sandwich shop.

Sam pulled the Impala around the corner and waited. His patience was rewarded when he saw Dean emerge in a full-body banana outfit complete with big red floppy shoes and a tray of samples for passing pedestrians. Quickly grabbing his Camera phone, Sam headed across the street for the maximum video vantage point.

It was few minutes before Dean looked up to see his brother playing Spielberg across the street and then all hell broke loose.

"Sam," Dean bellowed, as he began to move toward Sam "What the hell do you think you're doing!" Dean took two steps before the floppy shoes decided to head in opposite directions, sending him careening into a family of four whose lunch went spilling into the street along with Dean and two other customers.

Sam knew he'd pay for it later but the sight of Dean in his full-on pissed off mode inside an 8 foot tall, giant, yellow banana costume amidst all that chaos made it worth while.

Dean finally righted himself to find the manager demanding his costume back and informing Dean, in a polite shout, that he was fired. Dean looked across the street and locked eyes with his little brother, his expression darkening. He watched as Sam slowly pointed at himself and then used his finger to draw an invisible 'number one' in the air.

The fake, haunted sandwich shop would be legendary in a long line of legendary pranks, and Sam had the video to prove it.

Three - Auto Parts Store

With his little brother laid out by a broken ankle, two broken ribs and doped up on painkillers, Dean decided it might be best to stay in Springfield until the doctor cleared Sam. Unfortunately, there were only so many nights he could hustle pool before the locals got wise. Which is why Dean found himself planted behind the counter at the local auto-parts store. Day one was a challenge, as even auto parts could not make retail fun for Dean. But on day two, things got more interesting with the arrival of blonde & scantily clad Staci, the Tuesday cashier.

Dean wasted no time. His velvety smoothness was working over time and he was rewarded with her creamy goodness by lunchtime. Dean had just backed Staci up against the wall in the employee restroom when he felt a hand spin him around, a fist connecting with his chin and his butt impacting the dirty bathroom floor.

The bulk of Sven, the store manager, loomed over Dean as he pointed a very chubby finger inches from his face. "What the hell do you think you're doing? I should fire..."

Before Sven could finish his statement, Dean launched himself from his position on the floor into Sven's rather flabby gut, sending him crashing into the opposite wall.

Dean loomed over Sven, "Now, you can fire me." With parting a smile toward Staci, who gave him the 'call me' sign, Dean headed for the door.

Looked like Sammy was going to be recuperating in the next town.

Four – Gardener

They had driven the last twenty minutes in silence before Sam finally asked, "What made you think you could be a gardener?"

"What, you don't think I know how to mow a lawn?"

"When have you ever mowed a lawn, or trimmed a hedge for that matter?"

"That's not the point, Sam," his voice starting to take on that deep growl of annoyance. "I didn't know about the guard dogs and I had a limited amount of time to get the area cleared."

"They were poodles, Dean, and you could have worked around them."

"No way, they charged me, and the big one peed on my leg. I was completely justified."

"Even so, I don't see your solution as the only option."

"Well, you weren't there until the end, were you college boy. It's not like I hurt them."

Sam had to admit it had been a surreal scene he'd stumbled upon when he came to pick up Dean. The three poodles, legs wind-milling in the air, were safely hanging from homemade slings in a tree while Dean finished mowing the lawn.

"No, you just strung them up like furry piñatas. I mean seriously, Dean, what were you thinking?"

"Doesn't matter, it counts as a win," Dean smiled remembering the look on Sam's face when he'd arrived. "I got the job done and I got paid before she found the dogs and fired me."

"I give up!"

One time Dean Quit – Mechanic

They were stuck in this podunk town for a least another week but Dean wanted, no needed, to stay busy; and the mechanic job was just the thing. Messing with cars was a form of relaxation to him and, right now, he needed to be anywhere that wasn't a hotel room with his pissy little brother.

Calvin, the shop owner, asked a few probing questions and had him fill out some routine paperwork before pointing him toward a waiting Chevy. Dean was in heaven. Sure, Cal seemed to hover a lot but Dean figured he was just checking up on the new guy. The shopped closed at 6 pm and Cal literally had to push him out the door with a promise of work tomorrow.

The next day, Cal's hovering and leaning in wasn't easing up. After the second time Dean slid out from under a car to find Cal staring at his crotch, he knew he hadn't been hired for his skill with a wrench.

The curse of being ridiculously good-looking, Dean knew, was that guys had often found him attractive. Still, he'd never swung that way and, no offense to those that did, he had no desire to experiment. If this were a bar or some public place, he'd simply turn away and the guy usually got the message. This was different. This was his boss and Dean wanted to keep this job. As the day went on, Cal continued to invade Dean's personal space and Dean kept quiet. Gritting his teeth, he forced himself to focus on the Ford truck at his station, but the joy of the first day was gone.

By the time Cal stepped behind him to place a friendly hand on his shoulder that slipped down to caress the small of his back, Dean had had enough. He turned and gave Cal one of his patented 'I will cut you looks' and watched in satisfaction as the smaller man backed away hands held up in surrender.

Immediately, Dean's features softened at Cal's obvious discomfort. In the end, Dean thought it best to get his pay and leave the job behind.

Cal agreed and headed toward his office. He returned a few minutes later with a white envelope and held out his hand. Dean shook Cal's hand without hesitation and took the envelope.

Smirking as he walked away, Dean didn't wait to see the expression on Cal's face when he opened the note Dean had left behind in that handshake. The name and phone number were Sam's. Dean might not swing that way but God knows Sammy needed to get laid and Dean thought Cal might be just the guy for the job.