From Homestar Runner Wiki
Sickly Sam is the Old-Timey version of Strong Sad and is apparently a destitute victim of the Great Depression. Visually, he bears little resemblance to his current self, save for a more stylised version of Strong Sad's "soft-serve flip", and his personality is even more down-trodden than that of his modern-day counterpart. While Strong Sad is Strong Bad's brother, Sickly Sam does not appear to have any relationship with Old-Timey Strong Bad. In That a Ghost, Old-Timey Strong Bad doesn't even seem to know who Sickly Sam is, misidentifying him as the ghost.
Sickly Sam appears to have a partially exposed skeleton and wears a dirty Potate sack. When he's denied what he needs (which is very often), he vanishes into a cloud of dust. He also seems to have an adverse effect on inanimate objects that come in contact with him. Both his feet are cold, but his left foot is colder than his right, and his legs are very fragile and fall apart when he tries to dance. When he eats Old-Timey Strong Bad, he claims that it's the best meal he's ever had in his "extremely long life". None of the other characters seem to like him, and The Homestar Runner refers to him as the gang's "worst friend". To highlight his utter hopelessness, he buries himself alive on Tuesdays. On the plus side, he's good at dancing the Charleston.
Another Old-Timey version of Strong Sad (pictured to the left), which looks much more similar to the modern Strong Sad, appears being blasted out of a circus tent on Main Page 10. However, since this predates Parsnips-A-Plenty, it is clear that that design was scrapped in favor of Sickly Sam.
 Quotes of the Week
|Sickly Sam's Quotes of the Week|
|Strong Sad variations|
|Sickly Sam | Hot Tub | The First Decemberween | Lil' Strong Sad | Saddy Dumpington | The Deathly Pallor | Anonymous | Prancibald | 2046 Strong Sad | S. Sad|