Ike Barinholtz, Fred Armisen, Andy Richter, and More Try to Help Bobo Craft His ‘Ultimate Question’

Some spend their summers on the beach or at the pool, but for longtime Stern Show caller Bobo, his was spent trying to come up with the “ultimate question.” Bobo, whose calls to Howard have been considered lackluster in the past, recently received help from some bold-faced names in hopes of becoming a better inquisitor.

In audio heard Tuesday, the first coaches to pitch in were celebrity superfans Andy Richter, Fred Armisen, and Ike Barinholtz. After Bobo ran through a couple of questions, he was immediately met with confusion and critique from the comedy professionals. “What is the question?” Ike, who Bobo confused with frequent guest Eric Andre, wondered.

“Avoid the yes-no,” Andy suggested after Bobo proposed asking about Howard’s painting. “Take the topic and think of a way where it’s more of a conversation starter … I wish I had been here 30 years ago just to give you that note.”

“I could hear the advice going in one of Bobo’s ears and then out the other,” Howard noted after hearing the advice. “I wish Andy, Fred, and Ike would call into the show, not Bobo … they had some good questions.”

Actor Michael Rapaport was even more direct in his session with the caller. “Wipe your ass with that question,” he said bluntly. “You’ve had all summer to come up with a question, that’s what you want to ask Howard Stern?”

“Survivor” host Jeff Probst took a much gentler approach, encouraging Bobo to ask Howard which he’d choose: love or success. “If you were to ask a question like that, no matter which way Howard goes, there’s a conversation,” Probst said before giving Bobo a pep talk. “This is the biggest moment in your Stern career, Bobo. Imagine you come up with a question, and you ask it, and when the whole conversation is over Howard says, ‘… Bobo, well done.’”

On the phone Tuesday, Bobo revealed he learned from all his tutors. “They were all instrumental … Michael was a little rough but … I did come up with the golden nugget of a question,” he said before asking Howard what helped him become a great communicator.

“I don’t want to criticize the ultimate question … [but] it’s an obvious answer,” Howard responded. “What made me a great communicator, if you will, is the amount of hours I put in … and, also, that allowed me to become more of myself on the air.”

“The one thing Howard can do that you can’t is he self-critiques,” co-host Robin Quivers observed. “He doesn’t think everything he does is brilliant as soon as he does it. He crafts it whereas you just spit it out.”