Dressage is that one equestrian event without running, or jumping, or anything even remotely exciting happening. It's basically horse ballet, and while that sounds like it could be really pretty funny, that's because you're imagining it with the horse wearing a tutu. That doesn't happen with dressage.
No! Put the funny hat on the horse, not the rider! Such a missed opportunity, dressage.
Most importantly, dressage looks incredibly easy. But let's be generous, and assume it's one of those sports that is only meant to look easy. Like it only looks easy when it's done by highly trained elite athletes. These are horses after all, who are, as near as I can tell, some kind of combination between a dog and a bicycle, neither of which is terribly intelligent. Getting a horse to walk in a straight line has got to be a lot tougher than it looks.
But what really gets dressage on the Easy Sports list is because it's evidently only practiced by princesses and other people who can afford to spend a million dollars on a dog-bicycle. The 1 percent, essentially. Everything comes easy to these assholes.
#2. Beach Soccer
Sports are regularly added and dropped from the Olympic slate, which presents an obvious opportunity for us, the chair-centric medal seekers: the chance to compete in a sport where the competition may not be that deep. Obviously one of the conditions the IOC looks for when considering which sports to admit is the strength of competition, but it's unlikely that any new sport is going to have the same breadth of talent as, say, swimming. As an example, the very first gold medalist in snowboarding tested positive for marijuana, which is famously not considered to be a performance-enhancing drug, excepting sports where hands-awareness is crucial.
So look at the list of newish Olympic events and target one of those. This year there's women's boxing, so if you're a lady and into punching ladies, maybe look that up. Or consider beach soccer, which is a potential candidate for a medaled event in Rio in 2016.
You know. Soccer. Just on a beach.
Although most nations will surely be competing for who can lose the least badly to the Brazilians, that still leaves two medals to aim for. And compared to more established sports, it'd probably take only mild subterfuge to get a position as a backup beach soccer goaltender. You've got four years, folks; try it out! Get yourself a bronze tan to go with your silver medal to go with your always golden synchronized diver nailing.
#1. The Easiest Sport of All
So let's take what we've learned so far, and deduce the easiest sport to medal in. It should be team-based, to accommodate the hope that your teammates will do all the work for you. It should, strictly speaking, not exist yet, to account for the fact that winning medals is easier if no one is competing against you. And it should involve minimal physical fitness, to account for the fact that you're reading Cracked right now. So, after punching all of these factors into the Cracked Supercomputer, we get:
Four-Man Synchronized Horseshoes
Being the fifth man in a four-man Olympic horseshoes team is, at present, the easiest possible route to an Olympic medal. The only difficult thing about this is the fact that the sport is nowhere near close to existing yet, a fact that the IOC may get a bit hung up on when considering it for an upcoming Olympics. But even that isn't that hard to get around, because lest we forget, the IOC is spectacularly corrupt. A few diamond-encrusted horseshoes sent to the right people will surely overcome any such difficulties.
Or, failing that, a few sturdy, horseshoe-callused-handed handjobs for the right people.