This presents an interesting conundrum. Monsanto doesn't trust anyone who proposes a Monsanto employee drink a cup of Roundup because ostensibly they're afraid the cup is something other than Roundup. People who want to propose this "prove it" don't trust Monsanto to supply the cup of Roundup because they're afraid Monsanto will just give some colored, scented water that only looks like Roundup.
The actual Roundup product toxicity is from the inactive ingredients used as a carrier for the glyphosate [1]. Supposedly pure glyphosate itself is low toxicity. If (and this is a big if) the LD50 for humans follows mice models [2], at the highest amount of glyphosate required of 10,000 mg/kg, then the average human at 70 kg would require 700,000 mg of glyphosate to incur a 50% chance of a lethal dose. That is 0.7 kg solid form glyphosate, well over what we might find in a cup that is roughly diluted to the concentration levels one finds in the least concentrated form of Roundup. The lower end of the animal models is rabbits, acute dermal LD50, at 2,000 mg/kg, five times lower, 0.14 kg solid form glyphosate for that average human.
If there are 540 grams glyphosate per liter of Roundup R/T 540 Liquid Herbicide (the term of art is "540 grams acid equivalent per litre", please, some chemistry hacker out there correct my quantities, I'm sure I'm getting this wrong), then a US customary cup of this kind of Roundup contains 127.76 g glyphosate. I chose this kind of Roundup because it looks like the least concentrated. The rabbit LD50 toxicity translated to a 70 kg human is 140 grams. The mouse LD50 toxicity translated to a 70 kg human is 700 grams. That cup is uncomfortably close to those levels for me, if my numbers are close to the ballpark; I sure as hell wouldn't drink that cup if my numbers are correct. I welcome corrections.
[1] http://www.roundup.ca/_uploads/documents/RT540_label_Mar2014...
[2] https://en.wikipedia.org/wiki/Glyphosate#Humans