Damon's first Oscars appearance (and win!) in 1998 featured him smiling from ear to ear throughout the night – and for good reason. The star was up for twin awards that year for Best Actor and Best Original Screenplay for Good Will Hunting.
Coming off a win for best screenplay at the Golden Globes – and an adorably funny shout out to his father ("Dad, I got a better seat than Jack Nicholson!") – the 27-year-old Damon and best friend Ben Affleck were in shock for most of the evening.
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Both men brought their moms as their dates to the show, and Oscars host Billy Crystal couldn't help but make a crack about baby-faced Damon's inclusion in the Best Actor category.
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"Matt Damon must feel like he's playing on the seniors tour," he said of the category, which featured veteran actors such Nicholson, Robert Duvall, Peter Fonda and Dustin Hoffman.
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While Damon lost the Best Actor award to Nicholson, he and Affleck looked thrilled as they accepted the award for Original Screenplay.
Damon also made it clear he wasn't upset about losing out on the Best Actor award. One of the best lines of the evening came after one reporter asked the much blonder, blue-eyed Damon which Academy Award he wanted more: Best Actor or Best Screenplay.
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''Are you kidding me, man?!'' a beaming Damon said. ''I've never even been here before. I didn't care!''
Affleck then quipped, "He just wanted a job, sir. Thank you."
Damon even offered to share the win with his friends back home celebrating in Boston.
"This round is on me," he said, "Send me the bill."
Watch our Live from the Oscars Red Carpet show on PEOPLE.com starting at 5:30 ET/2:30 PT on Feb. 28 – and the 88th Academy Awards at 7 ET/4 PT on ABC. Click here for a handy ballot of this year’s Oscar nominees!