The Other Side

We're searching for the funniest president -- but focusing on laughs can obscure the less-pleasant parts of a president's legacy. For example, lots of the early presidents had slaves. And no one had more than George Washington.

So let's get into it! Our guest is Azie Dungey. Currently a writer for "The Unbreakable Kimmy Schmidt," Azie is also the creator and star of the "Ask a Slave" web series from 2013. She worked as a costumed interpreter at Mount Vernon, and the series puts a comedic (and thought-provoking) spin on her experiences. Can you use comedy to teach people about slavery? Does the stain of slavery ruin Washington's image? And, oh yeah, was Washington funny?

• "Ask a Slave" website
• Slavery at Mount Vernon
• Azie Dungey on Twitter

MUSIC: Hail Columbia, "Shorty George" by Count Basie and His Orchestra, "Washington Squabble" by Claude Hopkins and His Orchestra

The search for the funniest president continues! Herbert Hoover unfairly takes the rap for the Great Depression ... but if we look past all that economic moping, was he actually a funny guy?

Tom Schwartz, the director of the Hoover Library and Museum in West Branch, Iowa, helps us find out. We discuss how Bert's Quaker upbringing shaped his self-expression, review some of his truly amazing accomplishments and explore his special (and humorous) connection with the youth of America.

• The Hoover Library and Museum
• Hoover's writings online (free!)

MUSIC: Hail Columbia, "The Quaker" by the Erroll Garner Trio, "Fish Fry" by Benny Carter and His Orchestra

Big Jay Oakerson headlines the club May 13-15. We asked him to do a podcast, and true to his style of comedy he just sat down and started having a conversation. It's pretty amazing to watch the tightrope act live ... you get a unique comedy experience show after show.

Also chatting: feature act Mike Finoia, who is Jay's buddy (and roommate). We talk about the Philly scene, what got them into comedy, and Jay's upcoming Comedy Central special.

The search for the funniest president continues!

James K. Polk is legendary for getting stuff done -- his four years in office featured a war with Mexico and tremendous territorial expansion of the United States. But did Polk do it with a smile?

John Bicknell, the author of "America 1844," joins us to chat about the 11th president. We talk about Polk's legendary work ethic, what made him so driven, and whether humor EVER found its way into his White House. He won one election as a dark horse ... is there any chance he'll be elected funniest president?

• "America 1844" on Amazon
• John's bio at Watchdog.org
• John Bicknell on Twitter

MUSIC: Hail Columbia, "Charlie Horse" by Charlie Spivak and his Orchestra, "Tennessee Twilight" by the Eddie Condon Orchestra

The search for the funniest president continues! Chester Arthur

But if we've giving him a shot at the title, we need to think

We get context for the "bearded age," the peculiar 50-year span

It's a hair-raising discussion. HA!

MUSIC: Hail Columbia, "Fine and Dandy" by Teddy Wilson and his

When you work in a specialized field, you ALWAYS have to keep on

Cindy is back on our stage May 4!

Ian Bagg is one of the great road warriors of comedy -- stand-up

Ian tells us how his experiences playing hockey helped shape his

The search for the funniest president continues! Today, most

Our guest is Jon Lurie, a professor emeritus of legal history at

MUSIC: Hail Columbia, "Super Chief" by Count Basie and His

The search for the funniest president continues! Martin Van Buren took the rule book for American politics, set it on fire and wrote his own. He more or less invented the notion of professional political parties, then used his amazing creation to get Andrew Jackson elected president. When Jackson retired, MVB succeeded him in the White House.

But was he FUNNY? Journalist/historian/author James Bradley is a co-editor of Van Buren's papers -- he knows "Old Kinderhook" cold. We talk about the comedy Van Buren would have grown up with in his father's tavern and the ways he practiced humor to his political advantage. Most important, we talk about MVB's political revolution -- and the generations of presidential humor that became possible as a result.

MUSIC: Hail Columbia, "Martin on Every Block" by Lionel Hampton and his Orchestra, "Ultrafox" by Django Reinhardt and the Hot Club Quintet

The search for the funniest president continues! FDR rewrote the rule book for presidential behavior ... including the use of humor. His deeply personal connections with voters, reporters and fellow world leaders produced a lot of laughs (and also a bunch of government programs, but who's counting?).

Bill Harris of the FDR Presidential Library and Museum helps us get inside Roosevelt's head. We talk about the origins of Roosevelt's sometimes corny humor, his willingness to be silly in serious settings, and his calculated use of laughter to control certain situations. Plus we break down two bits of comedy associated with FDR: the famous "Fala speech," and the Broadway musical "I'd Rather Be Right."

MUSIC: Hail Columbia, "Happy Days Are Here Again" by the Casa Loma Orchestra, "Hyde Park" by Duke Ellington and his Orchestra.