| 2026-08-30 | Like Scrooge McDuck |
| 2026-05-30 | Rolling in it |
| 2026-04-07 | Rolling in it |
| 2026-01-31 | Opulent |
| 2025-09-29 | Very well-off |
| 2024-03-24 | Preposterous |
| 2023-12-24 | Like Ebenezer Scrooge |
| 2023-09-25 | Calorie-laden |
| 2023-04-19 | Loaded ("Diving Into the Wreck") |
| 2022-01-01 | Oil-___ |
| 2021-12-02 | Like chocolate mousse |
| 2021-11-26 | Like angel investors and devil's food cake |
| 2021-06-27 | Laughable |
| 2021-05-17 | Like the 1% |
| 2021-04-08 | Deep-pocketed |
| 2021-03-26 | Like sauces in French cuisine, typically |
| 2020-12-03 | High-G.D.P. |
| 2020-06-15 | Like a billionaire |
| 2020-04-07 | Like Mr. Moneybags |
| 2019-12-28 | Like triple fudge brownies |
| 2018-07-19 | Worth a great deal |
| 2018-06-29 | Amusingly ironic |
| 2017-07-03 | Wealthy |
| 2016-12-20 | Decadent, as cake |
| 2016-06-12 | Rolling in it |
| 2016-01-24 | High in calories |
| 2015-07-16 | "That's ___" (sarcastic response) |
| 2013-07-04 | Laughable |
| 2013-06-20 | End of the word ladder |
| 2013-05-29 | Calorific |
| 2013-05-19 | Laughable |
| 2012-10-02 | Like the people on the Forbes 400 list |
| 2012-01-03 | Among the 1%, so to speak |
| 2011-03-13 | Rolling in green |
| 2011-02-23 | Rolling in it |
| 2011-02-01 | High in calories |
| 2011-01-03 | More than well-off |
| 2010-11-09 | Filthy ___ |
| 2010-10-06 | Full of calories |
| 2009-09-18 | Sumptuous |
| 2009-05-05 | Very chocolaty, say |
| 2007-01-09 | Very sweet and full of calories |
| 2006-09-15 | Highly amusing |
| 2006-09-04 | Having megamillions |
| 2006-02-03 | Loaded |
| 2005-11-27 | On easy street |
| 2005-04-14 | Full-bodied |
| 2005-04-05 | Rolling in dough |
| 2004-08-24 | Rolling in the dough |
| 2003-01-26 | Loaded |
| 2001-03-11 | Loaded |
| 2000-01-25 | Rolling in dough |
| 2000-01-11 | Like chocolate-chocolate cake |
| 1999-06-19 | Deep |
| 1999-02-20 | Mellow-toned |
| 1998-02-02 | Rolling in dough |
| 1996-08-05 | Rolling in money |
| 1996-06-27 | Lucky in the lottery, maybe |
| 1996-06-12 | Too amusing for words |
| 1996-04-16 | Rolling in dough |
| 1996-01-24 | Opulent |
| 1995-06-28 | Like a German chocolate cake |
| 1994-05-31 | Imitator Little |
| 1994-04-21 | Abundantly supplied |
| 1993-11-25 | Well-off |