Holland took us all the way back to Tim Cheveldae, Detroit's goalie from 1988 until 1994. He mentioned Bob Essensa and then Mike Vernon, Osgood, Dominik Hasek, Curtis Joseph and Manny Legace before going back to Hasek and then Osgood.
There's only one Martin Brodeur, one Patrick Roy, one Roberto Luongo. The Wings haven't had anyone like that on a long-term basis since Terry Sawchuk, but they've still won the Stanley Cup four times in 11 years with guys like Vernon, Hasek and Osgood.
Yet, every single season Holland gets asked if his team's goaltending is good enough?
"That has been an age-old question for us," he said. "I've lived with it for 15 years."
This season, though, the question has some real validity to it as the Wings enter the playoffs with Osgood slated to be the starter in Game 1.
Statistically speaking, Osgood put together his worst regular season in his 15-year career as he finished with a 3.10 goals-against average and .887 save percentage. Osgood struggled so mightily at times that Detroit gave him a 12-day break between starts in February to find his game.
In his second game back from the sabbatical, he gave up four goals on 14 shots to Nashville. He shut out the Blues on March 3 with 22 saves, but, four days later, Columbus scored seven goals on him.
"This year has really tested me more than any other because I always felt I have been on the verge of turning things around and then something else would happen and something else would happen," Osgood told NHL.com. "I would get on a big roll again, and then something else would happen."
Through it all, Osgood said he's learned how to be tougher, how to compete harder. The competition from backup Ty Conklin brought about a lot of his motivation.
"If he wouldn't have played like he was, it would have been real tough on me this year," Osgood said of Conklin.
Fortunately, the Wings were still winning at a decent clip, even when Osgood was stumbling this season.
The Stanley Cup Playoffs are here and it's time for Osgood -- a three-time Cup champion, including twice as the starter -- to prove himself again.
"I'm not kidding myself, I haven't played well this year," Osgood said. "This is one of those years where things haven't gone right; but the one thing that it has taught me is to keep working, dig down deep and keep believing in the same thing you do everyday. If anything, it has made me work harder and it's going to make me better in the long run.
"To be totally sincere, I really feel I'm going in the right direction heading into the playoffs. I feel that is going to be my time."
Osgood can believe that because he thinks he knows where he went wrong this season.
"One of the biggest mistakes I made is I started the year thinking I had to play exactly the same way as I did in the playoffs last year and I really didn't have to," he said. "I just had to play when I was told to play and practice hard when I didn't play. That's what I did when I came back after the lockout and that worked out for the best."
He said that same philosophy is why he was so good in the playoffs last season.
Babcock went to Osgood during the second period of Game 4 against Nashville in the Western Conference Quarterfinals. Hasek was struggling and the Predators were on the verge of evening the series at two games apiece, which they eventually did.
However, Osgood got the start in Game 5 and never gave the net back to Hasek. He won his first nine starts of the playoffs and finished with a 14-4 record and a 1.55 GAA, backstopping the Wings to the Cup for the second time in his career.
"When I went in in Nashville, people would ask me, 'What were you thinking?'" Osgood said. "Well, I really wasn't thinking anything because I was confident that I had done what I needed to do to get ready and I didn't put any extra pressure on myself.
"I did (put on extra pressure) this year," he continued. "I was thinking, 'Oh my God, I have to play exactly the same way I did in the playoffs last year and if I don't do it people are going to think I'm not as good as that or maybe it was fluky.'"
Osgood compared the feeling to a guy that signs his first lucrative long-term contract.
"A guy that never made a ton of money before is now on a huge contract and he's trying to play up to that contract," he said. "It's impossible. I put too much pressure on myself. I don't have to do that. I just have to be solid, make the saves I need to and control myself back there."
That's all the Red Wings have ever asked for from Osgood -- or really any of the 20-odd goalies that have inhabited the Detroit crease since 1990-91, when the aforementioned Cheveldae became the No. 1.
"We won the Stanley Cup last year and our goaltending was solid, just solid," Holland said. "We didn't give up a lot of chances and when we needed the key save we got the key saves. That's the way we're built. That's why we have $20 million or so on defense. It depends on how your team is built."
The Red Wings are still built around their and the questions about their goaltending won't go away.
It bothers Osgood because he says he has fought so hard to change the perception; but, at this point, it may be a lost cause. It's not something he's too worried about, either.
Osgood knows he has to bounce back from a sub-par regular season. To do so, he regularly thinks about Games 5 and 6 of last year's Stanley Cup Final against Pittsburgh.
With the Stanley Cup polished and ready to be brought out to the Joe Louis Arena ice, Osgood gave up a game-tying goal to Max Talbot with 34.3 seconds to go in regulation of Game 5. The Penguins won the game on Petr Sykora's goal in the third overtime.
Two days later in Pittsburgh, with questions swirling around him, Osgood rebounded by stopping 20 of 22 shots as the Wings won the Cup with a 3-2 victory in Game 6.
"People ask me, 'How are you going to bounce back?'" Osgood said. "Well, I don't believe there is a harder game to bounce back from (than Game 5). I don't feed off of what happens in the regular season. I feed off of that.
"You have to be honest with yourself," he later added. "I know I have to play like I did last year in the playoffs. If I don't, the chances of us winning aren't very good."