A thing to keep in mind, apparently Strong Sad is in the 18-24 demographic while Strong Bad isn't.
Yup yup, I took that into account with my guesstamations:
in his 5,000s
The Cheat was apparently discovered after
Strong Bad met Homestar - I see him as the youngest. But since he's been Strong Bad's lacky for a long time obviously, I think he's still well in his years. Also, he is a smoker*.
I think of homsar as younger, partly because he was created after most of the other characters were established. I also think he should be in the same peer groupd as Strong Sad since they hang out. A 19-year-old could mingle well with a 21-year-old
Strong Sad is obviously younger than Strong Bad, and apparently in the college-age demographic. Since Strong Sad and Strong Bad were showing hanging out as kids, I don't think they could be too
far apart in age. Making Strong Sad much younger than 21 would pull Strong Bad into the 18-24 demographic too. Besides, since he's become less whiney in the more recent cartoons, he seems to have grown a little out of a depressing teenager attitude and into a apathetic college kid attitude.
Homestar is obviously old enough to drink cold ones, so over 21. He's old enough to be out of skool (if he ever went to any college?) and has a job. He shouldn't be too much older than Strong Sad, or too much younger than Strong Bad.
Marzipan is obviously older than Homestar. Can't you just feel it?
PomPom is probably older as well. Just because, ya know, he's a cool guy that the rest seem to look up to for the newest hip things. Even Strong Bad wants advice from him, and I just can't see him publicly
admitting the coolness of a guy younger than him - he'd be more likely to argue that PomPom wasn't cool
if he were younger.
Strong Bad at 26 puts him at an age that would still be a peer to Homestar, PomPom, and Marzipan, and just slightly out of Strong Sads demographic. If he were too much older than Homestar, then his rivalry with him would seem kinda creepy I think. At 26 he's old enough to be an 80's child which fits in with his music and video game taste.
Strong Mad should be closer in age to Strong Bad than Strong Sad, since they have a closer relationship as partners in crime. But Strong Mad seems distanced from the others, I think 30 seems like an understandable age guesstimate.
Poopsmith... I just feel like he's around the age of 37. Personally, I just kinda get that he should be at an age that he could be the King of Town's son. *shrug*
Bubs and Coach Z's ages are based on the ages of my mom and dad. I think it suits them.
Senor is over 60 as shown in "rated." But not as old as the KoT.
KoT is in his 60s as shown by "space program" - but I think of him as older than that, so I put him as close to 70 as I could while still staying in the 60s.
Eh Steve! Kinda looks like Anciet Egyptian style. So, over 5,000 years old.