Most bands don’t play 2,000 shows over the course of their career, but then again, most bands aren’t Umphrey’s McGee.

The Chicago-by-way-of-South Bend, Indiana sextet is ringing in their 1,999th and 2,000th shows Friday and Saturday, respectively, at the Orpheum Theater. Upon first hearing this, many would wonder, why Madison for such milestone shows?

Looking at Umphrey’s career and history, however, it becomes a bit more apparent. The group has played 34 documented shows in Madison dating all the way back to 1999.

The group’s first trip to Madison came in April 1999 and was at the Mango Grill, which sat where University Square does now. A little more than one year later, they returned to play Angelic Brewery, the same building that now houses Red Rock Saloon.

The fact that Umphrey’s has advanced from these small, now-defunct venues to playing two sold-out shows at the Orpheum speaks to both their longevity, as well as growth in popularity.

The group couldn’t be happier about coming back to play the Orpheum, the group’s keyboardist Joel Cummins said.

“The Orpheum, now that they’ve made it right … is really an outstanding room,” Cummins said. “Not only for us as a band, but for the fans too.”

This undoubtedly factored into the group’s decision to have their milestone shows in Madison.

“We’re looking for the kind of places where we can really throw a party and everybody can have a good time. The Orpheum is one of those places we can put on a great production and do it right,” Cummins said.

But the Orpheum isn’t the only thing that brought them back.

“We were just saying that the Wisconsin fans are second to none as far as the energy they bring to the table for our shows,” Cummins said.

Because Umphrey’s is an improvisational band, there’s no telling what the crowd is going to get on either night. Umphrey’s is known for their covers and mash-ups. With the special circumstances of these shows, it’s hard to not wonder if Madison fans are in for something special.

A big reason why Umphrey’s has been so successful and enduring is their ability to keep their sets fresh and experiment.

“We rarely ever repeat ideas or concepts,” Cummins said. “I don’t think we’d still be doing this if we had.”

Aside from being masters of their craft, the members of Umphrey’s are just as much workhorses. Cummins said that when not traveling or performing, the group is almost always working on new stuff to keep shows fresh. Between rehearsal, soundcheck and the final pre-show warm-up, the group has little time for anything besides dinner. This commitment to preparation is part of what makes their live shows special.

The band has no delusions as to what fans expect from them.

“Our business is throwing a party for everybody else,” Cummins said about Umphrey’s shows.

Despite the show’s inevitable party-like atmosphere, Cummins said it should be equally powerful and life-affirming.

“[The show] is a really intense, enveloping experience, that at the heart of it is all about celebrating life.”