| 100% | AWINK | 5 | Harry Connick Jr.'s "___ and a Smile" |
| 46% | CROON | 5 | Emulate Harry Connick Jr. |
| 46% | SHE | 3 | 1994 Harry Connick Jr. album |
| 46% | CROON | 5 | Sing like Harry Connick Jr. |
| 45% | SHE | 3 | Million-selling Harry Connick Jr. album |
| 45% | ACOKE | 5 | "Have ___ and a smile" (old slogan) |
| 43% | TRUMAN | 6 | Harry S. ___, 33rd President of the U.S.A. and the last (so far) to sport a beard in office |
| 42% | JILL | 4 | Model Goodacre who's married to Harry Connick, Jr. |
| 40% | CHUCKLE | 7 | Response between a smile and a belly laugh |
| 40% | TRAITS | 6 | Dark hair and a warm smile, for two |
| 39% | TIVO | 4 | Brand whose mascot has a smile and two antennas |
| 38% | DIE | 3 | "___ With a Smile" (song by Lady Gaga and Bruno Mars) |
| 38% | CONNICK | 7 | Harry __ Jr.; jazz singer, actor and TV host |
| 38% | LOVE | 4 | "We Are in ___," Grammy-winning album by Harry Connick Jr. that was featured in "Cheers" |
| 38% | MEGHANMARKLE | 12 | Former actress who's marrying Prince Harry, and receiving a royal title, today: 2 wds. |
| 38% | WITH | 4 | "Die ___ a Smile" (2024 hit for Lady Gaga and Bruno Mars) |
| 38% | CONNICK | 7 | Actor and "Australian Idol" judge Harry ___, Jr. |
| 37% | CAMPOUT | 7 | Activity with a tent and s'mores |
| 37% | AIMLESS | 7 | A smile’s terribly haphazard |
| 37% | AIMLESS | 7 | A smile's terribly random |
| 37% | AIMLESS | 7 | A smile's turning random |
| 37% | WCFIELDS | 8 | "Start every day off with a smile and get it over with" |
| 36% | TWO | 3 | TV's "___ and a Half Men" |
| 36% | MLB | 3 | Org. for O's and A's |
| 36% | WCFIELDS | 8 | *He said "Start every day off with a smile and get it over with" |
| 35% | OPRAH | 5 | She conducted a 2021 TV interview with Harry and Meghan |
| 35% | AIMLESS | 7 | A smile's turned out to be random |
| 35% | DADS | 4 | ___ Root Beer (Barq's and A&W rival) |
| 35% | ALERS | 5 | Yanks and A's, e.g. |