| ARSENIOHALL | Talk show host who won a season of "Celebrity Apprentice" |
| GREIG | Radio host who made it to the top five in the 2015 season of Celebrity Apprentice Australia, Mel ___ |
| LEEZA | Talk show host who won "The Celebrity Apprentice" in 2015, familiarly |
| JONSTEWART | Former "Daily Show" host who won a Spoken Word Grammy for "Earth (The Audiobook)": 2 wds. |
| JOANRIVERS | American comedienne and TV personality who won the 2009 series of Celebrity Apprentice in the US |
| RACHELMADDOW | MSNBC host who won a 2021 Grammy for the audiobook of her nonfiction book Blowout: 2 wds. |
| JIMMYFALLON | TV host who won a Best Comedy Album Grammy |
| LENO | TV host who won a Mark Twain Prize for American Humor |
| WADEBOGGS | Red Sox Yankees and Rays third baseman (1982 1999) who was a first ballot Hall of Famer but never won a season MVP award: 2 wds. |
| DAVIDORTIZ | Twins and Red Sox DH (1997 2016) who was a first ballot Hall of Famer but never won a season MVP award: 2 wds. |
| DEREKJETER | Yankees shortstop (1995 2014) who was a first ballot Hall of Famer but never won a season MVP award: 2 wds. |
| TONYGWYNN | Padres outfielder (1982 2001) who was a first ballot Hall of Famer but never won a season MVP award: 2 wds. |
| RIVERS | Joan ___, comedian and television host who won an Emmy Award for her daytime talk show in 1990 (6) |
| DYLANLEWIS | Recovery host who won Celebrity Big Brother (5,5) |
| SPRING | Name, derived from a word originally used to refer to the origin of a stream or well where water rises naturally from the earth, for a season of the year (6) |
| DAY | A season of The Pitt takes place over the course of a single one |
| OMAROSA | The only "Celebrity Apprentice" participant to appear on a previous "Apprentice" season |
| DARA | First name of Mr O Briain, former Mock The Week host who won Taskmaster in 2022 (4) |
| TEN | Number of episodes in a season of "Curb Your Enthusiasm" |
| RING | Gift at the end of a season of "The Bachelor," usually |
