| Text | Length |
| Amateurish painting | 19 |
| Wipe, as tears | 14 |
| Unskillfully apply | 18 |
| Spread (on) | 11 |
| Splash on | 9 |
| Smear, like paint | 17 |
| Smear with grease or mud, e.g. | 30 |
| Smear on | 8 |
| Slap on, as paint | 17 |
| Produce amateurish art | 22 |
| Plaster; smear | 14 |
| Paint, in a way | 15 |
| Paint without trying to stay within the lines, say | 50 |
| Paint without precision | 23 |
| Paint with a sponge | 19 |
| Paint on Sundays | 16 |
| Paint none too delicately | 25 |
| Paint messily | 13 |
| Paint like an amateur | 21 |
| Paint like a toddler | 20 |
| Paint ineptly | 13 |
| Paint haphazardly | 17 |
| Paint badly | 11 |
| Fingerpainting | 14 |
| Do fingerpainting | 17 |
| Crude painting | 14 |
| Cover with wide strokes | 23 |
| Color crudely | 13 |
| Coat, as with plaster | 21 |
| Coat with plaster, say | 22 |
| Brush carelessly | 16 |
| Apply, as plaster or paint | 26 |
| Apply, as plaster | 17 |
| Apply, as fingerpaint | 21 |
| Apply roughly | 13 |
| Apply paint crudely | 19 |
| Apply ointment | 14 |
| Apply in a slapdash way | 23 |
| Apply artlessly | 15 |
| Did some finger painting | 24 |
| Painted sloppily | 16 |
| Painted crudely | 15 |
| Painted amateurishly | 20 |
| Did some fingerpainting | 23 |
| Applied hastily | 15 |
| Applies crudely, as paint | 25 |
| Paints unskillfully | 19 |
| Paints amateurishly | 19 |
| Smears on | 9 |
| Fingerpaints | 12 |
| Uses finger paint, for example | 30 |
| Tries fingerpainting | 20 |
| Smears on messily | 17 |
| Plasters, e.g. | 14 |
| Plasters | 8 |
| Pats (on), as plaster | 21 |
| Paints undaintily | 17 |
| Paints roughly | 14 |
| Paints messily | 14 |
| Paints badly | 12 |
| Lotion application units | 24 |
| Finger-paints | 13 |
| Colors crudely | 14 |
| Applies sloppily | 16 |
| Applies makeup, sometimes | 25 |
| Applies crudely | 15 |
| Dishearten | 10 |
| Cause to cower | 14 |
| Overcome with fear | 18 |
| Lessen the courage of | 21 |
| Cause to lose courage | 21 |
| Make shake, maybe | 17 |
| Treading lightly, perhaps | 25 |
| Fazes | 5 |
| Disheartens | 11 |
| Causes to quail | 15 |
| Late-night name | 15 |
| Humorist Barry | 14 |
| Brubeck of jazz | 15 |
| Jazzman Brubeck | 15 |
| Jazz great Brubeck | 18 |
| Host Letterman | 14 |
| Garroway | 8 |
| Comedian Chappelle | 18 |
| Brubeck or Garroway | 19 |
| Wendy's founder Thomas | 26 |
| Talk show host | 14 |
| Late-night nickname | 19 |
| Jay's rival | 15 |
| Brubeck | 7 |
| Rival of Jay | 12 |
| Letterman's nickname | 24 |
| Jay's competition | 21 |
| Comic Chappelle | 15 |
| Barry or Brubeck | 16 |
| 1993 Kevin Kline movie | 22 |
| Rocker Matthews | 15 |
| Pianist Brubeck | 15 |
| Letterman of late-night | 23 |
| Letterman nickname | 18 |
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