I'll throw a couple cheapies out there (and no, I don't work for JR but i did stay at a Holiday Inn Express last night). If you smoke smaller/short cigars you can routinely find boxes/bundles for less than $60.

$1 Flor de Oliva bundles run about $28/$30 bundle of 25
$1 Consuegra bunles run about $25/$30 bundle of 25

$2 Maria Mancini (JR weekly special has 40 for $60 ending tonight Jan 17th)
$2 What about Perdomo Exclusivo? JR has boxes for under $60 (they throw in 8 freebies)
$2 Belinda and Belinda Black come to mind.
$2 Indian Tabac
$2 Puros Indios (check out Cigars International)