| Highest-grossing film of 1988 | 29 |
| Highest-grossing film of 1996 | 29 |
| Highest-pitched woodwind | 24 |
| Highest-priced boxing ticket | 28 |
| Highest-ranking angels | 22 |
| Highest-ranking Boy Scout | 25 |
| Highest-ranking personnel | 25 |
| Highest-ranking USN officer | 27 |
| Highest-ranking, in a way | 25 |
| Highest-rated, as a hotel | 25 |
| Highfalutin, culturally | 23 |
| Highflier's hangout | 23 |
| Highland family groups | 22 |
| Highland fling participants | 27 |
| Highland Games necessity | 24 |
| Highland Games participants | 27 |
| Highland precipitation | 22 |
| Highland region of the U.S. | 27 |
| Highland Scot, for one | 22 |
| Highland Scottish clan | 22 |
| Highland terrier, briefly | 25 |
| Highland/lowland separator | 26 |
| Highlander with a wiry coat | 27 |
| Highlander's accessory | 26 |
| Highlander's bonnet | 23 |
| Highlander's dagger | 23 |
| Highlander's fling? | 23 |
| Highlander's headgear | 25 |
| Highlander's hillside | 25 |
| Highlander's negative | 25 |
| Highlander's old tongue | 27 |
| Highlander's pattern | 24 |
| Highlander's pouch | 22 |
| Highlander's pride | 22 |
| Highlander's purse | 22 |
| Highlander's refusal | 24 |
| Highlander's rejection | 26 |
| Highlander's reply | 22 |
| Highlander's skirt | 22 |
| Highlander's speech | 23 |
| Highlander's tongue | 23 |
| Highlander's uncle | 22 |
| Highlander's weapon | 23 |
| Highlanders and lowlanders | 26 |
| Highlanders' adornments | 27 |
| Highlanders' dance | 22 |
| Highlanders' group | 22 |
| Highlanders' hillsides | 26 |
| Highlanders' language | 25 |
| Highlanders' skirts | 23 |
| Highlanders' weapons | 24 |
| Highlands "Hardly!" | 29 |
| Highlands "huh-uh" | 28 |
| Highlands haberdashery | 22 |
| Highlands head covering | 23 |
| Highlands monster, familiarly | 29 |
| Highlands off Sandy Hook | 24 |
| Highlands relative of an elk | 28 |
| Highlands tourist spot | 22 |
| Highlands' refusal | 22 |
| Highlands' waterfall | 24 |
| Highlight for a cantatrice | 26 |
| Highlight in print, in a way | 28 |
| Highlight of many a western | 27 |
| Highlight of many operas | 24 |
| Highlight of some musicals | 26 |
| Highlight reel accompaniment | 28 |
| Highlight with a high light | 27 |
| Highlighted agenda item | 23 |
| Highlighted rte. on a map | 25 |
| Highlighted with vines? | 23 |
| Highlighter colors, often | 25 |
| Highlighter's ship? | 23 |
| Highlighter, essentially | 24 |
| Highlighters, for instance | 26 |
| Highly bullish market advice? | 29 |
| Highly charged, as a topic | 26 |
| Highly charged, as an issue | 27 |
| Highly collectible book | 23 |
| Highly constructed home? | 24 |
| Highly contentious situation | 28 |
| Highly controversial furs | 25 |
| Highly decorated Bradley | 24 |
| Highly desirable reviews | 24 |
| Highly developed region | 23 |
| Highly efficient carbon sink | 28 |
| Highly embellished style | 24 |
| Highly energetic person | 23 |
| Highly enthused, informally | 27 |
| Highly esteemed person | 22 |
| Highly excited by eagerness | 27 |
| Highly excited, in slang | 24 |
| Highly flammable liquids | 24 |
| Highly flammable object | 23 |
| Highly informal language | 24 |
| Highly intelligent group | 24 |
| Highly maneuverable warships | 28 |
| Highly opinionated sorts | 24 |
| Highly ornamented style | 23 |
| Highly personal art form | 24 |