| Trivia | Best Supporting Actor Oscar Winner |
| Beat out a co-star, an actor who previously won two Oscars and an actor who won one later. | |
| Starred opposite a former Best Actor and Best Actress winner in his winning film; both were also nominated for their performances. | |
| At the time of his win, shared his name with a president who left office two years prior. | |
| Portrayed Betty White's father on 'The Golden Girls' | |
| Won his Oscar exactly 40 years after he earned a nomination for his first credited role. | |
| Won his second Oscar by beating two supporting category winners, one past and one future. | |
| The first winner of the Best Supporting Actor Oscar. | |
| The only person to win an Oscar in a Kubrick film. | |
| Won his first Oscar at the age of 62; won his second at the age of 78. | |
| According to date of birth, the oldest winner. | |
| At 80 years, the oldest guest to appear on 'Dennis Miller Live' in 1999. | |
| Lost more than 30 pounds to portray a real-life person. | |
| The only male actor to win an Oscar in a Woody Allen film. | |
| The first British winner. | |
| The only winner with an alliterative first/last name whose initials aren't C.C. | |
| Won his first Oscar for playing a newspaper editor; won his second for playing a novelist. | |
| The last person to win two Best Supporting Actor trophies. | |
| This actor's winning film was his first of 11 onscreen match-ups with another supporting category winner. | |
| Won Best Actor 21 years before winning Best Supporting Actor; both films won Best Picture. | |
| Shares a surname with the winner from 55 years earlier. | |
| His other Oscar nominations came 38 and 39 years earlier. | |
| The first winner to portray a mobster. | |
| Oscar-winning hairstylist Paul LeBlanc worked with this actor to achieve a 'strange and unsettling' effect. | |
| The last winner to portray a police officer. | |
| First winner to later win the Best Actor Oscar. | |
| Starred opposite two actresses playing young/old versions of the same character; both were also nominated for Oscars that year. | |