I'm currently facing a problem with the Kendo UI MultiSelect widget for selecting an option more than once. For example, in the image below I want to select Schindler's List again after selecting The Dark Knight, but unfortunately the MultiSelect widget behaves more like a set than an ordered list, i.e. repetitive selection is not allowed. Is there actually a proper way to achieve this? Any workarounds?

That's the intended behavior of the multi-select control and there is no simple way to make it do what you want using the available configuration options. Possible workarounds are ...
Creating a custom multi-select widget
Something like this should work (note that I haven't tested this much - it lets you add multiples and keeps the filter intact though):
Demo here.
Using a dropdown list
Use a simple dropdown list (or ComboBox) and bind the select event to append to your list (which you have to create manually).
For example:
Then you could bind clicks on those list elements to remove elements from the list. The disadvantage of that is that it requires more work to make it look "pretty" (you have to create and combine your own HTML, css, images etc.).