Common multi-word phrases that nearly rhyme with toothless:

2 syllables:
booze bus,
fruit twice,
school bus,
shoot twice,
you thus,
blue pus,
ku klux,
move us,
truth must,
blue ice,
chew ass,
ruth was,
truth was,
blue blood,
blue thrush,
boot leg,
drew blood,
fruit cups,
group must,
new blood,
roof truss,
school must,
school twice,
shoot cuffs,
shoot ducks,
smooth tongue,
smooth young,
soul must,
tooth bud,
truth but,
truth can,
truth when,
use must,
you trust,
fuel is,
pool is,
rule is,
school is,
soul is,
tool is,
tooth is,
truth is,
cool as,
rule as,
rule has,
school as,
school has,
smooth as,
soul as,
soul has,
truth as,
truth has,
blue leg,
boot ups,
bruce douglas,
crew cuts,
fuel up,
hoop la,
knew just,
knew then,
new love,
rule on,
school on,
shrewd thrust,
soul on,
thou must,
too must,
tool up,
true love,
truth on,
truth trust,
tune ups,
you just,
you let,
you love,
you must

3 syllables:
consume twice,
fusion assay,
gloomy gus,
produce stress,
produce twice,
produced twice,
reduce stress,
renewed twice,
reviewed twice,
route twice,
stupid ass,
undue stress,
cuba is,
nuclease assay,
produce thrust,
pucca house,
remove lumps,
roofless house

4 syllables:
absolute roughness,
absolute trust,
diffusion assay,
dilution assay,
molecule is,
cupola house

Some other possibilities:

What's up with this "phrase rhymes" section?

This experimental new tab on RhymeZone shows you phrases that might be good matches for your multi-syllable query word. For example, the word poetry produces phrase rhymes like boba tea and swollen knee and hopeful he and moments we. Some of these (like "boba tea") are single conceptual units, while others (like "hopeful he") are sentence fragments. Both kinds of results may be useful when writing slant rhymes that cross line boundaries, which are popular in hip hop lyrics and musical theater. Typically, RhymeZone's phrase rhymes are assonant (share vowel sounds) with the query word, with some degree of consonant match as well.

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See toothless used in context: 47 rhymes, several books and articles.

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