Here is a photograph that has actually been discussed seriously by at least one author and on the Internet of course:
A Brazilian postcard c. 1932. Note the coincidentally Gray-like profile in the background; why this hasn't sparked outlandish theorizing yet is beyond me.
Information about this alleged supersnake is rather variable, never a good sign. Heuvelmans reports it to be 30m long and 60 cm wide with a weight of 2 tons. When it was getting killed under machine-gun fire, it reared up 9 meters to crush bushes and small trees. Murphy & Henderson gives a much more detailed report of a 32 m by 1.25 m 3 ton snake with "horrid huge eyes". Both connect it to the photo. Then there is this drawing I found on Cryptomundo (no indication of source) which gives the wrong date and re-imagines this photograph to look a lot more convincing. It should be obvious to everybody why the photo didn't turn out like the drawing; should being the key word. Tim Dinsdale (whom I suspect is behind the drawing) believed that the large eyes, mouth and "thickness at the sixth convolution" indicated this to be an unknown species. Murphy and Henderson, who literally wrote the book on giant snakes, suggest it was just decomposed. Oh, and although 2-3 tons sounds like a lot, a 100 foot anaconda would weight somewhere between 10-25 tons.
Welcome to the world of giant snakes and supersnakes! Giant snakes are very large specimens of known species, while supersnakes are proposed unknown species or subspecies that have obtained extremely large sizes. Like sea serpent reports, it has been suggested that some of the supersnake legends have some rather non-snake-like characteristics, further muddling things. This covers both Zoological and cryptozoological ground, although with anecdotal evidence and mysteriously vanishing physical evidence it is more in league with the latter. Despite little evidence supporting the existence of outsized snakes, an African supersnake hypothesis of sorts has been published in a peer reviewed journal fairly recently. I'll discuss this later, but let's get back to giant anacondas.
The green anaconda (Eunectes murinus) is apparently the most massive species of snake and is frequently associated with Amazonian waterways. Murphy and Henderson consider it a giant snake (i.e. known to exceed 20 feet/6 meters), but exactly how big it gets has been a matter of dispute. Pritchard's Rule anticipates a record-sized snake is 1.5 to 2.5 times as long as the minimum adult female length (10.5 ft/3.2 m), so 8 m/26 feet is the presumed maximum for green anacondas. It should be taken into consideration that the maximum sized snake should be nearly 16 times as heavy as the minimally sized one, making for a rather impressive range. Pritchard comments that anacondas are not a rare species and thousands have been measured, and surprisingly even 20 foot specimens are considered rare. Presumably the average is somewhere around 15 feet/4.5 m; I wish publications listed averages and maximal sizes separately - before writing this I was under the impression that 20+ feet was normal. As hinted at by the first report, there have been many reports of anacondas over 9m/30 feet, and some several times even that length. So were there ever really snakes that big?
Estimating the lengths of snakes is often difficult and prone to extreme exaggeration. When one Ralph Blomberg heard about a 12 meter snake skin from an Ecuadorian military commander he was rather disappointed to find out that it actually measured 6 meters. Writer Hyatt Verrill recounted an incident where numerous people estimated the length of a coiled anaconda at 20-60 feet long - it turned out to be a monstrous 19'6" (and 360 pounds/163 kg!). Savage-Landor recounted an incident where he estimated a snake to be 100 feet long judging by girth, although it turned out to be 18'5" after it was shot and measured. It had of course swallowed an entire deer and the author speculated that immensely wide trails had a similar cause. Then there is the case of Fragrant Flower, a python that allegedly measured nearly 15 meters in an Indonesian zoo which actually turned out to be 6.5-7 meters long. So effectively eyewitness accounts of giant snakes, even at very close proximity, cannot be trusted.
Teddy Roosevelt's famous offer of 5,000 dollars for a snake exceeding 30 feet has been collected, and it is doubtful that such a specimen will ever turn up. Murphy and Henderson speculate that anacondas in the rain forest may get 7-8+ meters (23-26 feet) in length due to their need to overpower large prey, although I doubt the species can now get much larger than that. There are lots of stories about animals in the not-too-distant past attaining very large sizes (2.4 m otters, super-gigantic basking sharks, et cetera), so, unless these are all exaggerations, perhaps the green anaconda and large pythons* reached somewhat larger sizes into historical times. But 40-50+ footers, well, they're probably too outsized to be any living species.
* The Burmese (Python molurus), Reticulated (P. reticulata), and African Python (P. sebae) are of comparable if not greater length than the green anaconda, which weights more though. Their stories aren't as frequently exaggerated, nor does the same "supersnake" type story occur.
The largest fossil snake is the 9.3-10.7 meter (30-35 foot) Egyptian Gigantophis garstini, so the usual prehistoric survivor paradigm in cryptozoology doesn't really apply here. This size range, at least the lower end, appears to be reachable by outsized pythons. If this is an average length for Gigantophis though, this implies that outsized freaks of this species could have been veritable supersnakes. There's no evidence of this of course. As far as we know, the green anaconda is the most massive snake we have good evidence of, well, sometimes.
It appears that very large anacondas, both real and not, may have gotten mixed up to some degree with reports of the Sucuriji Gigante. One Father Heinz both saw and collected stories of this cryptid, which he had once mistaken for a steamship. It is allegedly incredibly fast (10-15 times as fast as a boat), was very aggressive, had phosphorescent eyes (or eye in one case), had huge teeth in its lower jaw, and pushed around vegetation mats rather than move around it. The fact that it had its mouth open at all is noted as being unusual by Murphy and Henderson. They suggest that none of these characteristics are snake-like, but don't further suggest what it could be. Heuvelmans explicitly suggests that primitive whales may be behind reports, and some of Heinz's reports do resemble sea serpent reports. Murphy and Henderson follow with an account of an alleged 56 foot anaconda that also had phosphorescent eyes (and was allegedly killed). And if you recall from the very beginning of this post, the "giant" anaconda allegedly had glowing eyes again. I don't think that there's much to support the idea of non-snakes getting intertwined into things, it just seems like people added more "horrific" characteristics to an already gigantic and potentially frightening animal. There still is a remote possibility that the Sucuriji Gigante could have been from a fourth anaconda species or a subspecies of E. murinus. But like most things cryptozoological, there's very little evidence and a lot of speculation.
I won't pretend that I can make a conclusion on this matter yet. Animals obtaining notably larger sizes into quite recent times is a frequently mentioned tend, although one I have difficulty finding documentation of. There's also the idea of a Pleistocene relict subspecies/species, although if there ever was a larger species of anaconda, I don't see it continuing to survive without the megafauna it presumably preyed upon. Is it even plausible to have a larger anaconda? Presumably it would be a specialist tapir/manatee/boto/large caiman predator. And then there's the ability of people to exaggerate the length of snakes up to five-fold. The Sucuriji Gigante is even more mysterious than oversized anacondas, although hardly a notable cryptid in its own right. It could just be based off of incredibly exaggerated anacondas. I suppose all we can do is wait and see if some monstrous sub-fossil vertebrae show up, or not.
I've barely scratched the surface on giant snake and supersnake reports from the Amazon. I'd recommend my references, particularly Murphy & Henderson, for more information on these sorts of reports. While these aren't exactly the most plausible of reports, they still are rather entertaining.
And yes, there was that one peer-reviewed article on African supersnakes I have yet to cover...
References:
Heuvelmans, Bernard. On the Track of Unknown Animals. John Wiley & Sons Limited, third English edition, 1995.
Murphy, John C. & Henderson, Robert W. Tales of Giant Snakes. Krieger Publishing Company; Malabar, Florida; 1997.
References:
Heuvelmans, Bernard. On the Track of Unknown Animals. John Wiley & Sons Limited, third English edition, 1995.
Murphy, John C. & Henderson, Robert W. Tales of Giant Snakes. Krieger Publishing Company; Malabar, Florida; 1997.
Addendum: 
Señor McCormick's siesta is interrupted by an expertly (and painstakingly) rendered Sucuriji Gigante.