| 100% | HED | 3 | "I Guess ___ Rather Be in Colorado" |
| 95% | HED | 3 | "I Guess ___ Rather Be in Colorado" (John Denver song) |
| 95% | HED | 3 | "I Guess ___ Rather Be in Colorado," song by John Denver |
| 91% | HED | 3 | John Denver's "I Guess ___ Rather Be In Colorado" |
| 91% | HED | 3 | John Denver song "I Guess ___ Rather Be In Colorado" |
| 54% | YNOT | 4 | "Guess I will," in text-speak |
| 52% | GERALDFORD | 10 | "I guess it just proves that in America anyone can be president" |
| 52% | USAF | 4 | Military branch whose academy is in Colorado Springs: Abbr. |
| 52% | SHED | 4 | "_____ Rather Be With Me" (1967 hit) |
| 52% | SHED | 4 | "___ Rather Be With Me" (1967 hit) |
| 50% | TORNADO | 7 | "Bad luck, I guess … It was my turn, that's all. I was in the path of the ___" (quote from 18-Down) |
| 50% | ORNOT | 5 | " ... but I guess I could be wrong" |
| 50% | WHENINROME | 10 | "Well, I guess if everyone else is ..." |
| 48% | SPARROW | 7 | I'd rather be a __ than a snail, yes I would |
| 47% | ORNOT | 5 | "...well, guess I was wrong" |
| 47% | WOE | 3 | "___ is me!" ("I'm in trouble") |
| 47% | WOE | 3 | "___ is me!" ("I'm in distress!") |
| 47% | PREDICT | 7 | Guess that something will happen in the future |
| 46% | GULP | 4 | [Boy, am I in trouble now!] |
| 46% | SCRABBLE | 8 | Game in which I is 1 |
| 46% | INIMICAL | 8 | Sending in claim, I am opposed |
| 46% | IOTA | 4 | What I will represent in Greece |
| 46% | ASPENS | 6 | "Quaking" trees for which a ski resort in Colorado is named |
| 46% | EAST | 4 | "My heart is in the ___, and I in the uttermost west" |
| 46% | AREA | 4 | "I was in the ___ and thought I'd drop by" |
| 46% | AREA | 4 | "I was in the ___ and thought I'd say hi" |
| 45% | ELBA | 4 | Island in the "Able was I ..." palindrome |
| 45% | AREA | 4 | "I was in the ___, so I thought I'd drop by" |
| 45% | AREA | 4 | "I was in the ___ so I thought I'd stop by" |
| 45% | CAMO | 4 | Outfit you'd rather not be seen in |