Here's what rhymes with toothlessness.
ruthlessness Words that almost rhyme with toothlessness
uselessness rootlessness truthfulness youthfulness fruitlessness tunefulness luminous ruinous ruefulness spookiness humourlessness kookiness usefulness ludicrous bituminous luminance fruitfulness mutinous uveitis glutinous humanness untruthfulness humanise gruesomeness glutenous voluminous albuminous ruminants duelists dehumanise lutenists gratuitous humanists cumulus contumacious pugilists illusionists scrupulous lubricants fumigants nutriments unscrupulous communicants