| Hint | Song | Artist |
| Late lead singer of Big Star and The Hollies | |
| Artist, filmmaker and 60's icon; most famous work involved soup cans | |
| Baseball's all-time home run leader | |
| Sardonic actor most famous for his roles in Ghostbusters and Lost In Translation; was almost Batman | |
| Bespectacled forefather of rock n roll; died in a famous plane crash | |
| Comedic actor from acting family; claims to be 'winning', despite strong indications otherwise | |
| 'Classic' actor in the highest grossing movie in history (when adjusted for inflation), though won his only Oscar for a different film | |
| Legendary actor most famous for westerns, won 2 Oscars for directing. Michael J. Fox 'played' him in a movie | |
| 2-time NBA 6th Man of the Year, played for Mavericks, Pacers, Supersonics and Trailblazers; was on a recent episode of Parks & Recreation | |
| Former member of The Supremes with a very successful solo career; friend to Michael Jackson | |
| Member of Pearl Jam and solo ukelele artist | |
| Legendary Broadway actress also famous for her cameo in Airplane! | |
| Original Charlie's Angel and 1970s pinup; passed away on the same day as Michael Jackson | |
| Member of the Rat Pack; one of the most famous singers of all-time | |
| Famous actor and dancer; most commonly partnered with Ginger Rogers | |
| The Singing Cowboy; owned the California Angels baseball team for nearly 40 years | |
| The singer/songwriter, not the son of Michael Bluth | |
| Actress, Princess of Monaco; starred in Hitchcock's Dial M For Murder, Rear Window and To Catch a Thief | |
| Another Hitchcock blonde; most famous for being 'looked at' by Humphrey Bogart | |