When Monty Python Meets Winston Churchill Olbermann Takes Outlandish Humor, Brilliance To Msnbc

As his tag-team partner would say, Keith Olbermann is simply … gone.

Olbermann, like many of his witticisms, is veering off in a curious direction, trading in the profession he has spent his life pursuing.

The wisecracking ESPN anchor is scheduled to go one more round with Dan Patrick on “The Big Show,” the name the duo gave the Sunday night version of the popular “SportsCenter” telecasts.

Then, to steal one of Olbermann’s best lines - “For those of you scoring at home, or even if you’re alone” - he will leave sportscasting after 25 years to become a newsman.

That’s right - he’s going from deadpan to newsman at MSNBC.

“Guhhhhhhh!”

Some observers may be shaking their heads and a few may question his credentials. But those who think he’s just about sports and jokes should listen to him more closely.

“He’s one of the few people who can go from off-the-wall humor to doing a poignant and moving obit,” Patrick said of his sidekick the past 5-1/2 years. “We rarely talk sports. … His interests are far more ranging.”

Others who’ve rotated in Olbermann’s enigmatic and outlandish orbit agree that he can match wits with anyone on just about any subject, and that sometimes he can bounce between topics at dizzying speeds.

For example, in one conversation he might quote Winston Churchill, and mix in his theories on Watergate or Whitewater.

“Outside of sports, the guy knows a lot about everything. He can be quoting Churchill, and in the next instance can be talking about ‘Animal House.’ That’s what makes him so good,” said Mike McQuade, a producer for “The Big Show.”

Olbermann’s influences provide a clue to his “crack-the-other-guy-up” mentality.

He loves Monty Python and is a self-professed expert on Bob and Ray, a sardonic comedy team that performed from the 1940s to the 1970s. Olbermann taped about 150 hours of their shows.

Olbermann, a lifetime student of American history, also said he reads a lot of biographies, and is riveted by the cases of Lizzy Borden and Jack the Ripper. “What is better fiction than real life?” he said.

Olbermann’s home is filled with sports memorabilia, including bleacher seats from various stadiums and a baseball-card collection that now boasts about 35,000 cards.

“He’s different. He’s not your typical guy. He’s a weird, talented guy,” Patrick said.

Olbermann, a 38-year-old bachelor, was raised in an upper middle class household in Hastings-on-Hudson, N.Y., a small village just west of Yonkers. He is the only son of Ted, an architect, and Marie, a preschool teacher, both retired. Olbermann also has a sister, Jenna.

“I can only imagine what I was like as a kid,” Olbermann said. “My parents probably thought I was dropped off from another planet.”

Identified as a gifted child, Olbermann skipped the first grade. He quickly latched on to baseball as a natural outlet for his knack for math. His mom made trips to Yankee Stadium a summer ritual and the family still has season tickets.

At one point, though, Olbermann became so obsessed with the sport that he had to follow an odd-even rule at the dinner table that limited talk about baseball to alternate days.

Olbermann was honing his craft by age 13, calling hockey games for his prep school, under the direction of fellow student Chris Berman, now his well-known colleague at ESPN.

“It gave him a great deal of security,” said his mom, who was surprised by his early interest in sportscasting because of his shyness. “He didn’t have to hide his brightness because there were a lot of others who were pretty sharp.”

He enrolled at Cornell at 16, and spent his first day on campus driving around with his dad, looking for the college radio station. It wasn’t long before he took over as sports director, which allowed him access to Yankee Stadium

“I used to cut classes and go down to all the games,” said Olbermann, who was able to interview his heroes, alongside a crowd of well-known scribes, including Dick Young and Peter Gammons.

“Happy, happy. Joy, joy!”

Jim Burger, a Cornell classmate who was assistant sports director, recalls Olbermann had decided that a lot of people took sports way too seriously, and had already developed a style to lighten things up.

“From the get-go he knew he was doing something people enjoyed, being irreverent and unconventional,” said Burger, now a sports writer for the Reading Eagle and Reading Times in Pennsylvania. “He was just always willing and able to express a side of things that others didn’t see.”

Burger said what a lot of people don’t know about Olbermann is his charitable nature. Weeks ago, he donated $50,000 to his college radio station after learning it was in danger of closing.

“He just walked in the door and found out they had a crisis, and a day or two later, presented them with a check,” Burger said.

Olbermann had a few conditions. One was that the studio be named after Glenn Cornelius, the former program director and a friend of Olbermann’s who died last year. The other was that the station, at least once, play a tape saying it was a proud member of the “Olbermann Broadcasting Empire.”

“Everything I have came from this radio station. It’s not closing on my watch,” Olbermann said.

After graduation, Olbermann took his schtick to several big markets, including CNN in Atlanta, and stations in Los Angeles and Boston. But, paired with Patrick, he really came into his own at ESPN.

But the life of a sportscaster hasn’t been all fun and games. The frenetic pace of “SportsCenter” would wear anyone down. And the lifestyle that comes with being a sportscaster was getting to be a real grind.

“My level of enjoyment has dropped every year. The word ‘confined’ would give the wrong image, but I feel limited in what I can talk about. I feel like there are more important issues. I’d like to be able to talk about everything,” he said.

Complicating matters for Olbermann is that he doesn’t drive, due to a depth perception problem that relates, like a lot of other things in his life, to his passion for baseball.

Olbermann was racing to make a train on his way from a game at Shea Stadium in 1980 when he slammed his head into a metal plate.

Two years later he started experiencing side effects. At speeds over 15 mph, he can’t read depths. He relies on a car service or friends to ferry him around the rural setting of ESPN’s headquarters and his nearby hometown of Southington.

He doesn’t think his move to MSNBC is a risk and is especially excited about getting his own show.

“There will be times when I am stuck and have to do a lot more preparation than I do now,” Olbermann said. “But the scope, and the breadth, that’s what appeals to me.”

“Be there, Aloha!”