Jerry Kelly, Jesper Parnevik and John Cook are tied for third place at 4-under-par.
Winds blew heavily around the Waialae Country Club throughout Thursday's first round and Perry waited until late in his round to move up the leaderboard. He shared the lead at 4-under but dropped a stroke at the fourth, his 13th, when he missed a six-foot par save.
Perry birdied two of his last three holes to join Riley in first.
Last week at the winners-only Mercedes Championships, Perry played in the final group on Sunday and narrowly missed out on a playoff. He finished at 17-under par and fell short of joining two of the game's best, Sergio Garcia and David Toms, in a sudden-death playoff in a chase for his fifth PGA Tour title.
'I don't have any expectations,' said Perry, who lost a playoff to Mark Brooks for the 1996 PGA Championship. 'I'm trying to enjoy my last few years out here and I'm very comfortable.'
Riley is one player who is certainly comfortable in windy conditions. He resides in Las Vegas and plays a low-ball flight, which can certainly be beneficial in these conditions.
'Hopefully, it will blow like this all week,' Riley said. 'I'm a little more comfortable in it. I just like the challenge of being patient out there.'
Riley, like Perry, made his move to the top late in his round. He drained an 18-foot birdie putt at the 16th to move into a tie with Parnevik and Kelly, then converted a birdie at the last to earn his piece of the first-round lead.
Kelly birdied his final three holes, including a tap-in at 17 and a four-footer at the final hole, to take the clubhouse lead at 66.
'You have to be pretty confident of your setup,' said Kelly, referring to difficulties on the putting surface in windy conditions. 'It's got to be tough on the rookies. They haven't seen this course yet.'
Parnevik hit the most unusual shot of Thursday's first round. His drive landed against a tree at No. 10 and he took his driver and turned it around, playing his second left-handed. Parnevik missed the green short but pitched to 10 feet and saved par.
The colorful Swede, like his colleagues at the top of the leaderboard, caught fire late in his round. He knocked his tee shot to two feet at the 15th, wedged out of the rough to 12 feet on 16 and set up his final birdie at 18 when he ran home a five-footer.
Cook eagled the final hole to land in the group at four-under par.
Phil Tataurangi, Jonathan Byrd, Cameron Beckman and Stephen Ames share sixth place at minus-three.
Defending champion Brad Faxon, reigning PGA champion Toms, Scott Hoch and Mark O'Meara are among a group at two-under-par 68.
Garcia, last week's Mercedes Championships winner, struggled to a one-over 71 in the first round.