At last Sunday's Portuguese Grand Prix Hamilton's victory saw him become the standalone record holder in terms of most grand prix wins, with the six-time F1 world champion banking his 92nd career victory at Portimao.
He's also closing in on equalling Schumacher's record of seven titles, further fuelling comparisons between the two superstars.
Massa, an 11-time grand prix winner, has seen both up close having worked alongside Schumacher as part of the Ferrari system, including a season as teammates in 2006.
Hamilton, meanwhile, was a close rival of Massa's for a number of years, including their spectacular showdown for the world championship in 2008.
While conceding the best basis for comparison would be if he'd been teammates with both drivers, Massa feels he still has insight into how they stack up.
Speaking to the In the Fast Lane podcast, Massa said Schumacher's worth ethic, in terms of fitness and car set-up, was second to none - but that Hamilton is probably the more naturally talented of the two.
"It's very difficult to compare," he said. "I didn't race with Lewis in the same team. You really need to race with both of them in the same car, understanding the data, to compare one with the other.
"But both are completely amazing and talented and different, and complete drivers in so many areas.
"I would say on the technical side, Michael was in front. I don't really see Lewis working massively with the engineers, understanding everything on the technical side. I don't really think he knows [the car] 100%. But the talent and pace alone...
"Michael was training massively physically, Michael was very good on the technical side. I'm not sure [Hamilton] is exactly like that on the training side, on the physical side, but he's also not really like that on technical side.
"But he's making everything in the perfect way. Maybe even on the talent side, he's even over [Schumacher]. Because even if he doesn't work as hard, he can do everything in the perfect way."
Massa added Hamilton's raw ability was evident from when he first arrived in Formula 1 in 2007, and fought for the title despite being matched up against a two-time world champion in Fernando Alonso at McLaren.
"It was clear that Lewis was a very talented driver since he started," said Massa.
"He didn't win [the title] in 2007 because he had some mistakes, maybe some experience was missing in some races.
"I remember in China he crashed going into the pitstop, he just stopped in the run-off area. In the end he didn't win the championship because of some mistakes, and also the fight he had with Alonso in the same team.
"But it showed he had talent. He showed that he was different, he could beat any of the drivers. He showed straight away, in his first year, that even Fernando Alonso, also an amazing talent... he beat Fernando in his first year in Formula 1.
"In the end his numbers are showing his capacity, what he's able to do. The numbers keep showing, because he will beat all the records in Formula 1, victories and maybe this year he will already be the same number of titles as Michael Schumacher - which is something that is unbelievable."