somebody tryin' just to stay alive

Obscenely loud music is blaring from one of the first floor parlors, and it possesses a remarkable nautical quality that borders on the fucking epic.  You might be wondering the reason for these festive tunes, curious resident.  If you happen to be peering through your communicator or walking down the hall, venturing into the nearest open door, your vision is assaulted by a swath of colorful fabrics draped over the furniture, from the ceilings, along the walls.  The alluring glitter of gold winks up at you from piles on the floor, and a bust of someone who looks suspiciously like Edward Teach is bedecked in jewelry and scarves.
You might even see Dean Winchester, sporting an eyepatch and a large, plumed hat, lounging on a silk divan.  His jeans are tucked into heavy leather boots and he's wielding a flintlock pistol, cleaning the barrel with a chamois rag.  Pausing for one moment, he sets the gun aside and reaches over to pick up one of the gold doubloons scattered across the floor.  He then peels away the leafing and pops the chocolate money into his mouth, enjoying it with obvious relish.  Turning the music down as soon as it breaks to an instrumental interlude, Dean crosses his legs on the divan, getting comfortable.

He pulls out a hip flask, taking a swig and saluting the camera with his left hand - observant residents might notice that he appears to have only four fingers now.  Then he spreads his arms to welcome the adoring audience.

"All aboard, bitches."

A fast-paced guitar riff is playing, and the comm unit appears to be placed in its usual spot - the hulking desk by the window.  A little light is streaming in, and the room would be fairly dim if not for the tall floor lamp in the corner.  The music, a less-popular piece by Foreigner, thrums around the room and is soon accompanied by a heavy roll of steam from one side of the frame.  It's coming from the bathroom.  Once the lyrics start, though, the vocals are not those of American-born-and-bred singer, Lou Gramm, but Dean Winchester's low, throaty, almost-crooning voice.

"Hey baby, if you're feeeeeeeling down, I know what's good for you all day," The man hop-skips out of the bathroom, steam swirling around his head, clad in nothing more than a towel.  He's got a hairbrush in one hand and is singing into it pretty soulfully.  "Are you worried what your friends see?  Will it ruin your reputation lovin' me?  'Cause I'm a dirty white boy - dirty white boy!"  Dean slides along the wall, still wet, feet squeaking on the polished wood floor.  "Dirty white boy - dirty white boy!  Diiiiirty white booooy!"

He manages to make it through the second verse passably well, tossing clothes out of his bag here and there in search of, no doubt, a particular flannel shirt.  "I've been in trouble since I don't know when, I'm in trouble now, and I know - somehow, I'll find trouble again!  'Cause I'm a dirty white boy, diiiiiiiiiiirty whiiiite boy!  Yeeeaaaaaah!"

Once the instrumental break hits, so does the air-guitaring.

He appears to have noticed nothing at all aside from his singing and fairly poor excuse for dancing, but the show must be amusing.  Dean slides to a finish, whipping his head to one side and wiping his brow, tossing the hairbrush on the bed.  Panting, he glances casually over to the comm unit and realizes that the red RECORDING button is on.

Eyes widening to exponential proportions, he bolts to the camera with a muffled laugh and a well-placed "Shit", offering a broad expanse of chest before switching the camera off with a near-deafening click.