Establishing yourself as a principal member
 of The Second City, the legendary 
 improvisational comedy group that started in Chicago in the late 1950s, is not for the faint of heart. After all, it’s helped produce such comedic stars as Joan Rivers (class of 1961), John Belushi (’71), Dan Aykroyd (’74) and modern comics like Mike Myers (’88) and Amy Sedaris (’92).

“It’s kind of like winning the lottery — odds are not in your favor,” says Casey Whitaker, a 27-year-old up-and-coming improv sketch comic and a member of The Second City Touring Company. “It takes very specific skills to do what we do.”

Whitaker, who double-majored in arts administration and theater at the University of Kentucky, spent the last semester of her senior year at Second City’s Comedy Studies program in Chicago. That was six years ago.

Today, Whitaker has earned a place at the grownups’ table as a member of The Best of The Second City, a touring six-person ensemble featuring some of the best sketches, songs and improvisations from The Second City’s 
55-year history. The tour makes a stop at the Times-Union Center’s Terry Theater on Saturday, Jan. 31.

“This show is highlighting some of the more famous alumni like Steve Carell,” Whitaker says of the 90-minute, two-act sketch revue that’s about 80 percent vintage material and 20 percent modern improv. “And then we’ll talk about how they influenced us in between scenes and just doing a really old-school history archive to celebrate the 55 years.”

Whitaker, who says it’s Second City alumni like Rachel Dratch, Stephnie Weir, Tina Fey and Brad Morris who have influenced her, started training for her current role in 2009.

“I moved here to Chicago and fully immersed myself in the Second City-style of comedy,” she says. “I did the writing program and the musical conservatory. I took history of comedy and context of comedy. I’d performed all my life, but these classes opened my eyes and made me well-rounded instead of just knowing about being on stage.”

After completing her college-credit courses, Whitaker stayed at Second City to sharpen her skills within the building and to build on her improv, solo sketch and standup repertoire at Chicago institutions like The Playground Theater, UP Comedy Club and Zanies Comedy Club.

“Then you just start auditioning for the general auditions once a year,” Whitaker says of breaking into the coveted paid gigs at Second City. “And hope for the best, because it’s very competitive. I think it gets harder and harder every year because the class sizes keep getting bigger.”

The Best of The Second City tour features Whitaker and fellow improv sketch comics John Sabine, Jamison Webb, Kelsey Kinney, Jasbir Singh and Blair Beeken — taking them on a whirlwind trip around the United States through July.

“The chemistry and the amount of time that we’ve all been together and traveled together — I see these people more than I see my boyfriend or my family,” Whitaker says. “So you get a chemistry and you get a rapport. Being on stage together just seems normal and natural.”

One of Whitaker’s favorite sketches that the group will be doing is called “Pictionary,” and was created by Steve Carell. In it, hilarity ensues when two middle-aged couples battle during game night. Whitaker calls it a sketch that “helped shape a new genre of scene work.”

A mixture of archival pieces and straight-up 
improv means Whitaker and the other members of her ensemble have room for creative license.

“Our favorite part is at the end of the second act, when sometimes we’ll have enough time to do an improvised third act and then all six of us play together,” she says. “It’s live theater and the magic of it is that anything can happen. But at the same time, you always know that if anything was to go wrong, the five other people are there to support you.”