Back when the 40th anniversary was happening, I felt like there should have been three special character-based releases: One focusing on the main characters ("The Best of Friends" that came out later is pretty much the same idea), one focusing on old school supporting characters like Sherlock Hemlock, Biff and Sully, Roosevelt Franklin, and Guy Smiley, and one focusing on the most obscure characters of all time (like Professor Hastings, Dr. Nobel Price, Deena and Pearl, Leslie Mostly, and Aristotle). Of course there are some characters I wasn't too sure whether they would be among the "most obscure Sesame Street characters". Like Little Bird and Rodeo Rosie, who weren't on the show much but were heavily featured in books for years. And Bruno the Trashman, who was on the show for at least a decade but not much material has surfaced (though more has surfaced since 2009). And in fact I thought Dr. Nobel Price would be one of the most obscure characters, but then after the 40th anniversary DVD and book came out I started thinking that maybe he's not that obscure after all (though sesamestreet.org still doesn't have any clips with him). I know I made a list of what clips I'd include on those releases in another thread.
But Sesame Workshop could put out special iTunes releases of videos focusing on different characters, particularly obscure or supporting characters. Maybe put them under a special release (like they have for various multi-episode releases).
Like if they could make special 12-video collections (since all those season and "classics" collections have 12 episodes each), here's a few things I would do:
Sesame Street Classic Supporting Characters Vol. 1:
1. Roosevelt Franklin
2. Harvey Kneeslapper
3. Guy Smiley
4. Biff and Sully
5. Forgetful Jones
6. Two-Headed Monster
7. Little Jerry and the Monotones
8. Chrissy and the Alphabeats
9. Sherlock Hemlock
10. Don Music
11. Herry Monster
12. Prairie Dawn
Sesame Street Classic Supporting Characters Vol. 2:
1. Simon Soundman
2. Placido Flamingo
3. Dr. Nobel Price
4. Lefty the Salesman
5. Professor Hastings
6. Leslie Mostly
7. Deena and Pearl
8. Aristotle
9. Herbert Birdsfoot
10. Sam the Robot
11. Little Bird
12. Gladys the Cow
And a rundown of sketches I'd include for a few of those compilations:
Biff and Sully
- Five Feet High and Rising (with Johnny Cash)
- Yes and No Song (with Judy Collins)
- Biff and Sully share a drink
- Piano Scales
- One Thing leads to Another
- Biff Labels Paintings
- We Coulda
- This is My J
- Biff and Sully Get Angry
- Alphabet
- Sully Supplies Music
- Carrot Time
- Biff and Sully babysit Natasha
- This Song's For the Birds
- Roxy Marie's collections
- Biff hammers 19 times
Guy Smiley
- Pick Your Pet
- The Mr. and Mrs. Game
- What's My Part: Foot
- The Trading Game
- Beat the Time: Cookie Monster
- Here is Your Life: Tooth
- To Tell a Face
- Mystery Guest
- The Leslie Mostly Show
- Name That Sound: Grover
- The Letter of the Day Pageant
- I'll Love You in the Springtime
- What's My Job?
- The Audience Goes to Lunch
- Air
- Find That Shape
Dr. Nobel Price
- Foot Snuggies
- Slushabouts
- Tinker Table
- Umbrella
- Talky Stick
- Shagaphant
- Herman the Hoppity Hop
- Cupcake
- Soup Experiment
- Original Invention