Lots of open source software has gone for decades with the following license, without the wrath of god falling on them:

    Copyright (c) <year> <copyright holders>

    Permission is hereby granted, free of charge, to any person obtaining a copy
    of this software and associated documentation files (the "Software"), to deal
    in the Software without restriction, including without limitation the rights
    to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
    copies of the Software, and to permit persons to whom the Software is
    furnished to do so, subject to the following conditions:

    The above copyright notice and this permission notice shall be included in all
    copies or substantial portions of the Software.

    THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
    IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
    FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
    AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
    LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
    OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
    SOFTWARE.

It seems to me like you could just cut the paragraph starting with "Permission" and the words "and this permission notice" from the next paragraph, and you'd have the same protections, but for a closed-source project.

So yeah, I'm going to go ahead and continue to believe that these EULA's are definitely not written with the user in mind.

Has this ever actually happened? Particularly, has a software publisher ever lost such a case?

Class action? Like, on behalf of consumers? I can't think of any off-hand.

Cases on behalf of Larry Ellison, however...