By the end of his long career, bluegrass pioneer Bill Monroe had had as many banjo players in his employ as godfather Don Corleone had hired killers. In terms of banjo pickers, one could certainly say Monroe's cup runneth over, so it might be considered inevitable that in the last five years he wound up using the Cupp itself, as in Dana Cupp Jr. This bluegrass musician is most commonly credited as simply Dana Cupp, that is unless the project also involves his father, Dana Cupp Sr. The younger Cupp has been something of a torch on several instruments, heating up the still-active bands of senior bluegrass statesmen such as Monroe or the Osborne Brothers with whom Cupp has been playing guitar since the late '90s, alongside other veterans such as Leon Rhodes.
Cupp's status as Monroe's last banjo player was always a shaky affair due to the fact that the leader's Bluegrass Boys band was based out of Nashville, naturally, while Cupp lived in Michigan. Commuting was the name of the game and it wasn't always possible for the Cupp to be on the table everytime Monroe set the table for a gig. Cupp tried his darndest, even keeping a Nashville apartment with another bluegrass boy, guitarist Tom Ewing. Nonetheless, Cupp got grief galore from Monroe about his out-of-state residency. "He'd ask if anybody knew any banjo players that were man enough to move to Tennessee. Bill liked for a job to be covered," Cupp has recalled in interviews. The banjoist Rob McCoury sometimes did fill-ins, or there were sometimes strained situations such as the time young banjo whiz Bela Fleck got the call to show up for a hastily arranged television recording in Nashville that Cupp just couldn't be there to pour into. Musically there could certainly have been no problem, since Fleck knows the Monroe repertoire very well. But Fleck apparently made a big mistake by not wearing a suit. When Cupp later asked Monroe about the session, the elder statesman griped "That feller playin' the banjo -- he didn't know my numbers too good. And he wasn't dressed right a'tall!"
Cupp remains committed to the Michigan bluegrass scene. In the early part of the new millenium, he was serving as president of the Huron Valley Eagles, a bluegrass performance venue and organization. This is where one is most likely to find Dana Cupp Sr., who picks guitar with several local bluegrass outfits. The young Cupp has also performed with a variety of bluegrass bands including the Wildwood Valley Boys, Jimmy Martin and the Sunny Mountain Boys, and Pinetop.