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Bobby's library is the unofficial home base of many of the show's earlier seasons. If you keep an eye out, you can spy a handful of objects and pieces of furniture consistently popping up over this room's many appearances, but no two episodes have them arranged the same way. It's also very often that a piece of furniture will pop up in one episode only to be gone the next. Since 4.02 reveals that Bobby has a spare storage room upstairs, it's possible that's where he keeps most of this extra furniture.
There are two main iterations of Bobby's den. The first appears during seasons 1 - 3 and features less furniture, far more books, dark brown trim instead of black, and a different wallpaper (or no wallpaper in 1.22). The new wallpaper and black trim first appear in 3.10, and they can be seen alongside the new layout in seasons 4 - 7. This iteration of the library includes a large Persian rug, ornate wooden desk, twin book shelves to the left of the fireplace, a floor lamp and bookshelf to the right of the fireplace, the red couch in front of a set of bay windows, a half bookshelf in the far left corner, and a rolltop desk in the far right.
A large Persian area rug typically sits in the center of the room except for when some type of trap is being painted on the floor. A devil's trap can be seen on the ceiling in 1.22 and 6.20. Bobby's ceiling is beige and has wooden beams that match the rest of the trim.
The heart of Bobby's library is a wood-burning fireplace with green tiled surround and a black carved mantle where Bobby keeps books and random knick-knacks. In the later seasons, these include a small bulldog statue/bookend, a pewter pitcher with tankards, two silver trophies, and a wooden antique radio. Above the fireplace is a landscape painting framed by two electric wall sconces.
Decorations aside, Bobby's fireplace is also a practical hunter's tool. It's often used as a flame source for spells, and the iron pokers and other tools make for an easy handheld weapon against ghosts and specters. In 5.04, it's revealed that the center section of the mantle hides a secret compartment where he keeps a hunting journal similar to John's.
Bobby's carved wooden desk is first seen in 4.02 and, with a few exceptions, appears consistently up until it burns with the rest of Bobby's house. Earlier episodes (3.03, 3.04) either have a simpler table in its place or no desk at all (seasons 1 - 2).
Bobby's desk is a free-standing open pedestal desk with turned legs, lower shelves, and diamond-shaped carvings. Based on the style, it's likely from the late 19th or early 20th century. Similar desks can be seen here and here. The desk also has three shallow upper drawers, two deeper drawers on each pedestal, and a green stone top that Bobby uses as a chalkboard for spells. In 5.18, it's shown that Bobby keeps his Single-Action Army revolver in one of the drawers. In 6.15, Balthazar is rummaging through Bobby's drawers and finds a saint's bone underneath a false drawer bottom.
In seasons 4 - 5, Bobby tends to use a black flexible goose-neck desk lamp. Starting in season 6, he switches this lamp for a thin, rectangular, golden brown mid-century lamp. It could be assumed that this lamp was also destroyed in the fire that burned Bobby's house, but it actually shows up in Dean's bedroom in the Bunker in later seasons. So either the Men of Letters had the same lamp, Dean found a similar one at a thrift store at some point, or he was able to recover the lamp from the ruins of Bobby's house.
In seasons 1 - 3, the corner to the left of Bobby's fireplace contained the rolltop desk, a console table, and piles of books. This layout can still be seen in 4.01, but it is replaced in 4.02 with two matching bookshelves. The more left of the two bookshelves has a black gooseneck lamp clamped onto the top shelf, and sometimes a dining chair stacked with extra books is also pushed into this corner. Inside of Bobby's mind in 7.10, these shelves also hold framed photos of Bobby with loved ones as well as a book cut out to hide an elaborate crucifix.
Along with the matching bookshelves, 4.02 places a floor lamp, chair, and upright bookcase in the corner to the right of the fire place. This chair is typically some kind of living chair but is sometimes one of the wooden dining chairs that frequently get moved around the library. Next to the bookcase, underneath the bay window, is a red couch with a faint swirl pattern, carved wooden feet, and decorative panels on the arms. Bobby also owns a matching armchair (5.18, see above), but it is not usually seen in the library.
This couch is where Sam or Dean sleep while at Bobby's. If the both of them are there, Sam takes the couch while Dean sleeps on the floor (4.02, above). A gray blanket with faint stripes pops up in a few episodes as well as a striped pillow that appears to match the pillows on the cot in the panic room and in the linen closet upstairs (4.02). Various end tables and dining chairs get moved around the couch and used as nightstands or bookshelves.
To the right of the couch is a half bookshelf and console table stacked with books. In season 5, the console table is replaced with a vintage stereo cabinet. The stereo is used as a table and sometimes holds records (5.18 - 5.21), sometimes holds drawers and books, and sometimes holds a TV (6.04). A similar stereo can be seen here, though note that Bobby's has tapered legs. Also note that the wall sconce in this corner is the only one in this room that has two lights instead of one.
A pair of black pocket doors sits at the back wall of the library and leads to the kitchen. These doors slide into the wall rather than opening in- or outward, and are typically left closed. To the right of the doors is a black double light switch.
To the right of the pocket doors are typically a dining chair stacked with books, a black trunk, an upright blueprint holder filled with maps and plans, and at various times books and a radio. When this radio isn't on the trunk, it tens to sit on top of Bobby's rolltop desk alongside one of his many desk lamps and a decanter and glassware set. This desk is also where Bobby keeps a CB radio (used in 5.10).
Like Bobby's main desk, the rolltop desk is also either likely from the early 18th or early 19th century or is a replica of a desk from that period. It's always seen open and has an assortment of small drawers, cubbies, and cabinets on the desktop. It has a center drawer, and four drawers on the pedestals, and sits on casters so it can be easily moved.
As previously mentioned, there are several variations of Bobby's library within the show. In it's first appearance in 1.22, the library didn't have it's signature red wallpaper. The first wallpaper appears in 2.14 and has a toile pattern while the second wallpaper has a look closer to a jacquard or brocade. When we see Bobby's heaven in 10.17, the wallpaper (and rug and radio and couch...) is different once again.
Sometime between seasons 3 and 4, the dark brown wood trim in Bobby's library is painted black. In season 5, while Bobby uses a wheelchair, the couch is replaced with a twin bed with wooden headboard.
Bobby's library gets neater and cozier with every episode. What is little more than a dark place to stack hundreds of books in its first appearance is, by season 7, a proper living space with multiple light sources, tchotchkes, records, a couch, and pillows. No wonder it's the place where time and time again someone is brought when they need to stay somewhere safe and familiar. After years of being alone after his wife's death, it's almost as if reconnecting with his boys motivated Bobby to finally turn his house back into a home.
I felt the YouTube upload of the commercial could've been fixed up, so I got around to doing a small restoration/touch up of the recording. Bringing back the original color/saturation and aspect ratio.
"[Adrienne] showed up in Sioux Falls, and then she just grabbed me. And she said, 'Billie Joe?' And I turned around, and I was just – I had to remember what she looked like, because it just didn't register at first. I remembered her voice from the phone. She looked at her friend and goes, 'he doesn't remember me.' I felt like the biggest tool at that second."
