In the musical 1776 (I’m thinking particularly of the film version), there is a running joke that the Continental Congress regularly receives pessimistic dispatches from General Washington complaining of the miserable state of the continental army and despairing over the likelihood of defeat. In the movie, one member of congress says of Washington: “that man would depress a hyena,” later calling him “the gloomiest man on this continent“ and referring to his dispatches as “the most depressing accumulation of disaster, doom, and despair in the entire annals of human history.” I know it’s a little subjective, but are these descriptions (although obviously exaggerated) accurate in any way to Washington’s actual dispatches during 1776 (or any part of the war)? Is there any record of contemporaries making note of a pessimistic tone in his dispatches or of Washington having a reputation for this kind of communication? If nothing else, would such pessimism have been realistic to the actual situation on the ground in the summer of 1776?
Absolutely, without a singular doubt, yes.
In writing to John Hancock (then president of the Congress) on September 24, 1776, Gen. Washington opens with, "From the hours allotted to sleep, I will borrow a few moments to convey my thoughts on sundry important matters to Congress... We are now as it were, upon the eve of another dissolution of our army."
George Washington, as well as his staff and members of his inner circle within the Continental Army (notably the likes of Gen. Nathanael Greene), would regularly petition the Congress for provisions, men, guarantees of French tactical and strategic support, and so on. As may be seen with the opening statement of his September 24 letter, Washington had a flair for the dramatic, and, especially at particularly grim moments like that of Valley Forge, would take on a very melancholic and pessimistic tone when addressing Congress. He was also often apt to criticize members of Congress and the elite within New England cities, particularly Philidelphia, who did not practice war time austerity.
As dramatic as it may seem, however, Washington's urgent hounding of Congress was not without reason. While the Southern theater of the revolution seems to have been, from what I have gathered, carried by militia and opportunistic raiders from the backcountry and Appalachia, New England is where the Continental Army was the primary player (at least in the minds of the generals, both British and American). Plagued since the outbreak of the war by Smallpox, poor logistics, lackluster and unreliable recruitment drives, the Continental Army spent much of its time on the brink of disintegration. Even its most prominent victories, such as the battles of Trenton and Princeton (Washington's crossing the Delaware moment) were taken at a monumental risk to the Army's survival. Though, it must be said, such raids provided a more steady supply of provisions (captured from the defeated) than Congress ever did.
This is quite a loaded topic and I very much doubt any length of post could cover it in very much detail. So, I encourage anyone that is interested to delve into some of the listed sources here below:
If you would like to read about the personalities of the big names within the American Revolution I would recommend you start with John Ferling's Winning Independence. He expresses quite well just how dower Washington could sometimes be and gives good context for why that was.
For information about the impact of disease specifically on the Continental Army (as well as the civilian population) and how that moulded Washington's view of Congress, check out Elizabeth A. Fenn's Pox Americana.
And finally, if you're looking for primary source documents such as Washington's letter to Congress, Major Problems in the Era of the American Revolution, 1760-1791, edited by Richard D. Brown is a great place to start.
I hope this was a satisfactory answer to your question!