Possible Clues:

• 'Little Orphant Annie' poet
• Life of __ (carefree existence)
• The life of --
• The Hoosier Poet
• Poet who wrote 'An' the Gobble-uns 'at gits you / Ef you / Don't / Watch / Out!'
• "Harper Valley P.T.A." singer Jeannie C. ___
• The life of --- is carefree
• Hoosier poet
• He leads an easy life
• One with an enviable life