Fred Funk (66), Jay Haas (68) and Mike Goodes (68) were a stroke back, and Tom Watson (64) followed at 8 under. Defending champion Eduardo Romero, the U.S. Senior Open winner, was 5 under after a 65.
Langer, a two-time winner this year and the Champions Tours money leader, was 12 under after birdieing eight of the first 15 holes. But the German star dropped two strokes with bogeys at 16 and 18.
After finishing the front nine in 33, Langer put his extra-long putter to work, rolling in birdies on 10, 11, 12 and 13. As his 40-footer curled in at 11, he backpedaled across the green, pumping his fist.
Simpson, slowed by Lyme disease in the early 1990s, wrenched his back on the practice range during the U.S. Senior Open and had to withdraw from that tournament. On Friday, he began to experience pain that got progressively worse as he neared the turn. After bogeys on Nos. 9 and 11, Simpson managed to make an 8-foot birdie putt on 12, then called for tour trainer Doug Miller to work on his back.
With its particularly wide fairways and forgiving greens, Crosswater continued to yield low scores. Watsons 64 was the lowest score in the tournament since it moved to the course last year.
Funk plans to play the PGA TOUR full-time next year. Romero and Gil Morgan both eagled the 582-yard second hole. Morgan was 3 under after a 71. Corvallis native Bob Gilder holed out from the fairway for eagle on the 413-yard, par-4 fourth. He was 5 under after a 68.