I Thanked Boston Three Times: Why the 1998 Ben Affleck Matt Damon Oscar speech Still Stings

They have two Oscars each, but they'd rather forget the moment they won their first. Hollywood's ultimate duo, Ben Affleck and Matt Damon, recently opened up about the lingering embarrassment they feel over their 1998 Academy Awards acceptance speech for Good Will Hunting.

The Jackass Pact: Prep for the Ben Affleck Matt Damon Oscar speech

During an appearance on SiriusXM’s The Howard Stern Show on Monday, Ben Affleck cringed at his younger self. "I thanked Boston as a city three times. Was that necessary?" he asked. The reason for the chaos was simple: they hadn't prepared a single word. Matt Damon explained that they didn't want to look like 'jackasses' if they wrote a speech and lost.

When the win was announced, Damon was so overwhelmed he pushed Affleck toward the microphone, refusing to lead. This led to the famously energetic, albeit disorganized, moment that Damon says took many years to fully metabolize. Billy Crystal, the host that year, even improvised a song about them, a moment that Affleck says will stay with him forever.

From Outsiders to Netflix's 'The Rip'

The duo's chemistry remains a staple of the industry. Decades after their breakout, they're starring together in the Netflix thriller The Rip, set to release on January 16. Damon is also gearing up for Christopher Nolan's epic, The Odyssey, hitting theaters in July. It's a testament to a friendship that has survived the highs and lows of Hollywood fame.