I never liked Riley. From the very first, he was just too puppy dog charming, and it just occurred to me what was really wrong with the character. ("Excuse me, I was forgetting my manners in all the concussion.") The poor boy was suffering from brain damage! When I read later that the idea of Xander possibly the one to come out of the closet during Season 4 instead of Willow, I thought that 1) Larry might have actually seen the truth before anybody else did, and 2) THAT'S why he was originally brought on the show!
Seriously, my first impression the character was "Who's this jerk?" Riley never really grabbed me, (but then, neither did Angel when I first saw him. I've just never been able to get over the velvet jacket0 The first episode of "Buffy" that I ever saw was "Once More With Feeling," and the chemistry between Sarah and James was so dynamic that I immediately knew who the REAL "long haul guy" was supposed to be, even before I ever heard Xander's speech or laid eyes on Ol' Broody. Then, when he started pushing and shoving Spike around, even though he knew about the chip and, therefore knew that Spike couldn't defend himself, my opinion of him dropped even lower. Having been the victim of bullies in my younger days, I have never had anything but contempt for them. (I always really hoped that Riley could have shown up after Spike's chip had been removed just to see the look on Riley's face when "Ass Face" cleaned his clock properly in repayment for his previous actions)
Christian Cane would almost certainly have made a better Riley, especially if he had been able to have been able to keep the sinister element in the character. What Riley and the entire Initiative was doing in Sunnydale WAS sinister: capturing "Hostile SubTerranians" in order to build super soldiers is just about as sinister as you can get. Innocent farm boys from Iowa would not be the type to be involved with anything like that, and neither would someone so stupid as to not figure out what was really going on for as long as he did. I think Riley that should have been played exactly the same way as Robin Wood was at the beginning of Season 7: mysterious and sinister with an obscure background and a very ambiguous agenda. That would have been a Riley worth watching. As it was, he was just a permanent version of GI Joe Xander that first Halloween.