As a few people know, Sam and Max Season 1 didn't support widescreen resolutions in any shape or form, or even 5:4 resolutions.
According to a thread made by one of the developers at the Something Awful forums
Season 2 will support widescreen and 1280x1024. If your windows display properties shows it, Season 2 will do it.
When pressed futher as to whether it would be "proper" widescreen support (hor+) he stated
It's pure widescreen. As in the game was created with both widescreen and 4:3 ratios from the start.
So fear not regular and widescreen peoples! We accommodate all without being cheep about it!
The thread can be found here - http://forums.somethingawful.com/showthread.php?postid=333838540