Definitely the most painful.
An 18-hole playoff wasn't enough to decide a champion, so Woods and the unflappable Rocco Mediate went one more hole, where Woods finally prevailed for his 14th major championship.
"The guy's impossible to beat," Mediate said.
Woods did it on a wounded knee that may have actually gotten worse over five days and 91 holes of stress and strain, and laughter and pain, at Torrey Pines. Doctors told him not to play the hilly, 7,600-yard course, longest in major championship history.
No big deal, Woods insisted, even though the grimaces and winces on his face told a different story.
"You play through it and suck it up and get it done," Woods said.
This one might have come at a cost. Woods said he'd have to shut down his game for a while, refusing to rule out missing the British Open in a month.
But for the moment, he didn't care.
He was too busy delighting in the trophy he held for the first time since 2002 - the U.S. Open has been the toughest of the four majors for Tiger - and in the bright smile of his daughter, Sam Alexis, whom he scooped up after his victory and who didn't want to let go.
"Yeah, I think so," Woods said when asked if this major was his greatest achievement. "It's either this one or my first one. This week had a lot of doubt to it, to be honest with you. I hadn't walked 18 holes until the first round here since Augusta."
The knee injury was just part of the drama in Woods' seventh professional victory at Torrey Pines, the course where he played his first, regulation 18-hole round as a kid.
The fight Mediate put up was every bit as memorable.
He came into the week ranked 158, a qualifier who grabbed one of the last seven spots in an 11-man playoff earlier in the month.
He was not part of the conversation when the week began, and even after matching Woods through 72 holes, he was the ultimate underdog. This was the golf equivalent of Florida vs. Florida A&M in football, or Roger Federer vs. Aisam-Ul-Haq Qureshi, the 158th ranked player on the tennis tour. Everyone knows how those turn out, right?
But Mediate made this much more than perfunctory, falling behind by three after 10 holes, but making birdies on No. 13, 14 and 15 to draw even, then take a one-stroke lead.
"That hot streak was one of the most impressive things you can have on this golf course," Woods said.
Woods is no quitter, either, of course. "No way I was gonna bag it," he said, commenting on his pain.
He grinded out pars on 16 and 17 to stay within a shot of Mediate, then on 18, he served up another dose of drama, the likes of which he'd been providing on that hole all week.
After a 340-yard drive to the center of the fairway, he hit safely onto the green to give himself an outside eagle chance in case Mediate made a birdie. Mediate, however, teed off into a bunker and was forced to lay up.
Woods made a safe two-putt for birdie and when Mediate's 20-foot birdie try to win went past the hole, they were headed for sudden-death, which started on the par-4 seventh.
It was pretty much elementary from there - Woods hitting two solid shots to the green, while Mediate teed off into a bunker, then hooked his next shot wildly into the crowd.
The record will show that Woods needed 19 holes to win it on Monday, though maybe he really won it on No. 18 on Saturday ... and Sunday ... and Monday. He walked up to that tee box trailing each day, and made an eagle and two birdies to keep the tournament going.
"It's pressure, there's no doubt about it," he said. "I was nervous. But that means you care. You can try to use that energy as best you can to heighten your focus and then get in the right situation, and it worked out great for me this week."
Woods moved within four majors of tying Jack Nicklaus' record. He joined Nicklaus as the second player to win the career grand slam three times.
"It's hard to believe I've had this nice a run in my career, and hopefully it will continue," he said.
But as much as history, this victory was about this particular moment. It was one of those times when all the accolades - "great," "unbelievable," "best ever" - seemed appropriate, whether they were about Woods or the overall weekend of golf he was part of.
The U.S. Open, with its thick rough and glassy greens, is rarely this good and the 18-hole playoff is a dying breed because it hardly ever produces this kind of drama.
"It's usually one guy plays OK and the other guy plays really not that good," Mediate said. "It seems like today, it was just fun to turn the tables a little bit. I turned the table a little bit."
He'll move about 100 spots in the world ranking and won't have to worry about qualifying for this tournament next year - or the Masters in 2009.
But in the end, he goes down as a valiant loser and the answer to a trivia question: Who was the first player to lose to Woods in an 18-hole playoff? Or a 19-hole playoff?
There were times when it felt like the week would never end.
Asked how he pushed on despite the pain, Woods talked not about golf, but about workout sessions with his buddies, way back when.
"We used to always say 'How many more reps do you have?"' Woods recalled. "And the answer was 'Four. Forever,' And that's the idea. You just keep going. And there's no finish line. You keep pushing and pushing and I did that all week."