I'm no math wiz or data scientist. Here's my take though.
If the maximum allowable length for an Imgflip username is 32 characters and you only consider usernames that long, it's something like 39^32 possible usernames. Add in all the possible usernames that are 31 characters long, 30 characters long, etc.
That's a pretty big number.
Imgflip has been around for about 10 years. Presuming the current username rule (only a-z, 0-9, dot, dash, and underscore), if usernames were limited to a length of 4 characters, and Imgflip assigned available usernames to new users, we would have run out by now. If usernames were limited to a length of 5 characters and Imgflip assigned available usernames to new users, at the current rate of consumption there would still be many decades worth of possible usernames remaining.