Two days ago, while returning from the east coast on a business trip, I
heard an exchange between a plane going to OSH and the controllers in
Michigan. We were at 10,000 in an out of IMC and doing a large deviation to
avoid a line of thunderstorms.

The pilot going to OSH asked for an IFR clearance in the air to go to an
intersection near OSH (?) The controller patiently explained that a
reservation was required to get a clearance into OSH, although the pilot
didn't seem to understand what this meant, and kept asking for a clearance
to some intersection near OSH.

Finally, the controller said it wasn't going to happen, and offered VFR
advisories over the lake (roughly 80 miles). The pilot accepted this, and
proceeded to fly over the lake, between layers of clouds, at 4500 feet in a
single.

I mentally wished him luck.

While getting gas at my home base, the line guy related a story of a couple
in a clapped out ratty home built who wanted to leave at night to fly over
Lake Michigan, VFR. They said they did similar over water trips all the
time, and that they knew how to swim.

About five minutes after departure they returned, with a complete electrical
failure.

Most of the pilots I know would acknowledge that flying over Lake Michigan
in a single is a calculated risk, and would do it high, with lots of gas,
and perhaps with survival gear. Some won't do it at all in a single, since
the survival rate after ditching is very low. Most wouldn't do it at night
or in IMC.

Are there any other stories out there about questionable judgment flying
into OSH?