As his name suggests, the Man of Steel isn’t known for being on the receiving end of some embarrassing beat downs. While he has been defeated by characters such as Doomsday or Darkseid, there was nothing embarrassing about these fights, considering Superman at least somewhat held his own in those encounters, at least to a point. However, in issue 464 of the Adventures of Superman, written by Dan Jurgens and penciled by Art Thibert, Superman found himself on the losing end of a pretty embarrassing fight.
This 1987 comic starts by showing a drunk Lobo and two of his cronies trying to find their way into the Fortress of Solitude so that Lobo can take on the Last Son of Krypton. The comic then cuts to show Clark Kent adjusting to his new role as Managing Editor of The Daily Planet, with Kent even rejecting the advances of Lois Lane in this issue. Suddenly, Clark gets a splitting headache and instantly knows that someone has broken into his Fortress of Solitude, so the Kryptonian changes into his superhero costume and flies off to meet the intruders in the Antarctic.
The next scene shows Superman confronting the three drunk intruders, warning them to get out of his Fortress of Solitude before he has to use force. Naturally, Lobo doesn’t listen to Superman’s warning and then kicks Supes across the face, opening the fight between the two super powered characters. While Superman is able to land a few punches, it soon becomes clear that Lobo is far better at brawling than Superman, with Lobo taking the upper hand and smashing Supes through the walls of the Kryptonian fortress, even drawing blood from Superman.
After making a Superman-shaped hole in the wall, Superman is able to give Lobo the slip for long enough to reach a giant room with holographic capabilities. However, he can’t escape Lobo for long and the fight resumes, with Lobo continuing to be on top. Superman is thrown through another wall, revealing a safe containing kryptonite. The Man of Steel is obviously worried by this development and slips into a nearby battle suit to protect him from the radiation. Lobo mocks Superman for wearing armor in their fight, before then launching missiles at the armored Kryptonian. The next panel reveals a lifeless Superman lying atop the rubble of the battle armor.
While Lobo and his cronies are celebrating, it’s revealed that Superman, knowing he couldn’t defeat Lobo in combat, used the Fortress’ holographic technology to project an image of a dead Superman. Happy with the result, Lobo and the gang leave the Fortress.
It's not often that Superman isn’t able to use his powers to overcome an enemy, so this would’ve certainly been embarrassing for Kal-El, but it is certainly interesting to see Superman use his mind to overcome an enemy instead of his usual brute force.