The term ANNOY, AND THEN SOME can be broken down into four crossword solutions: RILE (4 letters), ENRAGE (6 letters), PESTER (6 letters), and IRK (3 letters). RILE means to make someone angry or upset, ENRAGE means to make someone extremely angry, PESTER means to bother someone persistently, and IRK means to irritate or annoy someone. All of these words are synonyms for the term ANNOY, AND THEN SOME, which means to cause someone to feel frustrated or irritated.