It could be a specific goal (his diving score against Tampa Bay comes to mind), a specific assist (him skating circles around Jason Spezza behind the net before setting up Sergei Gonchar), winning a Stanley Cup or two, or just a general memory (winning the NHL draft lottery).
But I wanted to know what Crosby's favorite memories are from his career. So I asked him.
"A lot of stuff in your rookie year sticks out just because you're going through everything for the first time," he told me. "The first goal against Boston. I remember that goal against Tampa that (Mark Recchi) passed to me. That was pretty cool. There was one against Phoenix that year, a backhander. I had some good ones early on."
Crosby then joked that he hasn't scored any dramatic goals since then. Of course, he was being casually flippant.
But of all the things from that rookie season in 2005-06, he remembers most the night he recorded his 100th point.
With two games remaining in his rookie season Crosby had amassed 97 points. Meaning he would need three points in the final two games to hit the 100 mark.
The only rookie in Penguins history to hit 100 points was Mario Lemieux.
The Penguins hosted the New York Islanders in the home finale at Mellon Arena. Despite the team finishing 29th in the league, fans filled the building for a standing room only capacity in the hopes that they could witness him reach 100.
And, as always with Crosby, he delivered.
Crosby picked up three assists in the game, the final coming near the end of the second period on a setup to Ryan Malone, to reach the 100-plateau. And the building exploded.
"The 100th point when 'Bugsy' scored a slap shot, I remember the building being sold out," Crosby recalled. "Looking back that was pretty special. I know it wasn't a winning season by any stretch, but we had some fun and made the most of it.
"The last game of the year, sold out rink, that was pretty fun. That one stands out."
Although there are endless memories from his career, Crosby also recalls some of the more obscure moments of levity.
"I remember the lights went out in one of those games. The Zamboni leaked everywhere in one game," he laughed. "I remember the goals, but I remember that stuff too."
Crosby has come a long way in the past decade-plus of his career. But he still looks back fondly on those early years and the bonds he made with his teammates.
"We had fun. We had a lot of young guys that were trying to establish themselves in the league, a lot of us grew up together," he said. "We were confident we were going to get better. But it was something we had to go through and we tried to make the best of it."
