Defending champion Billy Joe Tolliver shot a 3-under 69 to take the lead with 27 points in the modified Stableford scoring system, one better than four-time tournament winner Dan Quinn in the field of 81 sports stars and entertainers.
But the real action was with the players at the bottom of the leaderboard as they hacked and scrapped their way around the 6,707-yard course on the shores of Lake Tahoe.
Settle, who starred in HBO's 'Band of Brothers,' sliced a 5-iron on the 169-yard, par-3 17th hole into the boat, breaking not one, but two windows.
'That will go down in history,' said Settle, who started playing golf only a year ago. 'I don't think I've ever hit anything other than a tree. It was a tough day but I had fun.'
The scoring system awards six points for an eagle, three for a birdie, one for par, none for bogey and minus-two for double bogey or worse.
Tolliver had six birdies with three bogeys -- one with a penalty stroke because his caddie accidentally kicked his ball while stepping off a yardage. Tolliver drove the ball 340 yards on the par-5, 18th then barely cleared the pond in front of the green with his approach and got up and down for birdie.
'If it's one foot short, it's wet,' said Tolliver, the former NFL quarterback who has won the tournament twice. 'I live on the edge. It's hard being this good-looking and not live on the edge. Perfect face for radio.'
Quinn said he was determined to do well after finishing sixth in the $500,000 tourney last year. The former hockey player won in 2001, was third in 2002 and won back-to-back the next two years.
'There's nothing worse than getting on a flight to go home on a redeye out of Vegas on Sunday night when you had a chance to win and you know you should be able to,' he said.
Actor Jack Wagner and former quarterback Chris Chandler were tied for third with 23 points. Chandler had 18 points on the back nine, including a chip-in for eagle 3 on the last hole.
'That was a lifesaver,' Chandler said.
Tolliver said he hadn't heard about the broken boat windshield.
'That's the kind of word that doesn't travel fast, you know. It's not like a hole-in-one,' he said.
Mark White of Stateline was on the boat anchored just off the shore along No. 17.
'We had been sort of joking around about it before hand that there might be a chance of us getting hit. Then my buddy said, `Look out! Incoming!' And we heard the glass shatter. It just exploded. We couldn't believe it,' White said.
White said Settle came to the boat and apologized.
'He said he'd be happy to take care of the expenses. He was very nice about it,' White said.
Settle was paired John O'Hurley and Cheech Marin but said the comedians didn't rib him about it. But afterward, O'Hurley called the shot a 'flaming whoopsie.'
'I've seen broken windows on golf courses before but never on a boat,' he said.
It wasn't that strange to Chris Webber.
'I hit somebody in a boat a couple of years ago and they threw the ball back out like it was a home run at a baseball game,' he said.
Webber, who is betting Barkley $50,000 for charity that he'll better him, actually strung together consecutive pars in one stretch, including on No. 17 after he'd hit his tee shot 30 yards right and over the green then skipped his chip shot off the cart path to within 2 feet of the hole.
The previous hole he hit out of a greenside sand trap, catching the lip of the bunker before it trickled to 3 feet as Barkley shook his head and laughed in disbelief.
'That's what I tried to do,' said Webber, whose minus-22 points were nine better than last-place Barkley's. 'You've got to be able to use the whole golf course, the lip, the trees, everything.'