Kirk Douglas could put smiles on faces both while in character and out.
Unfortunately, Douglas passed just before the 2020 Academy Awards, to be held Sunday. Here's a look back at his best moments throughout Oscar history.
Lifetime achievement award
Despite being nominated for "Champion," "The Bad and the Beautiful" and "Lust for Life," Douglas never took home an Oscar for acting.
In 1996, 50 years after his first credited role, the Academy chose to honor the icon with a lifetime achievement award.
Ever the family man, Douglas dedicated the award to his wife, Anne.
Presenting with his son
The Oscars became a family affair in 2003 when Kirk and his son Michael presented the award for best picture at the Oscars.
"This is my son, Michael, he has two awards," said Kirk. "But I'm still young."
When Kirk Douglas opened the envelope containing the name of the winner, he ripped the slip in half, giving one part to his son. The two held their pieces together and read the winner in unison.
"I love talented women"
In 2011, Douglas took to the stage at the Oscars to present the award for best supporting actress after being introduced by Anne Hathaway.
"I want to thank Ms. Hathaway," said Douglas. "She's gorgeous! Where were you when I was making pictures?"
As Hathaway, now 37, fanned herself, Douglas said he had "something to confess."
"I love talented women," he said. "I'm crazy about beautiful women. And now, I'm going to give you five of them: the nominees for [the best supporting actress] award."
The award went to Melissa Leo, who asked him to pinch her upon winning.
Although he never took an Oscar home with him, Douglas received some love from the Academy with three nominations.
His first nomination came in 1950 for "Champion," in which he played Midge, an up-and-coming boxer.
Next, in 1953, he was up for the award for his role in "The Bad and the Beautiful," which won five other awards.
Douglas' third and final nomination came in 1957 for playing Vincent van Gogh in "Lust for Life."
A shoutout from Michael
Douglas' son Michael has won two Academy Awards himself, but his first for acting came in 1988 for "Wall Street."
When Michael nabbed the award for best actor in a leading role, he thanked his fellow nominees, his director and his father.
"I would like to dedicate this award to William Darrid, Diana Douglas Darrid, Anne Douglas and Kirk Douglas," Michael said. "My parents and step-parents who have been extremely supportive and loving to me over the years."
"In particular to my father, who I don't think ever missed one of my college productions, for his continued support and for helping a son step out of a shadow," he added. "I'll be eternally grateful to you, Dad, for that."