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I see this written a lot in advertising and amongst younger speakers - often as a standalone sentence referring to an act, product or activity. Can someone shed some light on how it's used and what exactly it means? To me it seems almost contradictory, but I guess I'm coming at it too literally.

Henry Firth
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"Leider geil"

means as much as that this is inappropriate and pointless, but still nice/awesome ("geil").

The expression ("leider geil") became famous through a song by Deichkind "Leider geil"

- turn on subtitles in English to understand better

This music video shows various incidents that are "leider geil". Watch the video, then you know more!

As example:

"Autos machen die Umwelt kaputt, doch ein schönes neues Auto ist leider geil"

...that means something like a new car would be very cool ("geil"), but since it harms the environment (CO₂), the word "unfortunately" is used, hence "leider geil". So it's a contradicting statement.

SwissCodeMen
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    It literally translates to "unfortunately awesome", does it not? "Cars destroy the environment, but a shiny new car is unfortunately awesome". – Vincent Nov 04 '20 at 19:25
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    Like many slang terms or jargon terms, it can also significantly shift its meaning once it enters more mainstream usage. The most famous example is probably the word "hacker" which, in the culture where it was coined, means something like "someone who builds cool things by creatively exploring interactions in complex systems", i.e. someone who creates, whereas in mainstream usage, it means the exact opposite, it is someone who destroys. – Jörg W Mittag Nov 04 '20 at 20:48
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    @Vincent: correct. It can also be used somewhat tongue-in-cheek when there is something that you feel you shouldn't like because it should be "lame", but actually is rather good, like if you are a hardcore Jazz fan and hate pop music, but totally dig Robbie Williams' big band swing album. You should hate the album because Robbie Williams represents everything you hate about the music business, but actually the album is "leider geil". – Jörg W Mittag Nov 04 '20 at 20:51
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    So, it doesn't necessarily have to be objectively negative as in the car example. – Jörg W Mittag Nov 04 '20 at 20:52
  • @Vincent The meaning becomes clearer if you put the words in a slightly different order: "Cars destroy the environment, but unfortunately a shiny new car is awesome". In a German sentence, "unfortunately" and "awesome" just happen to end up next to each other. – lyle Nov 05 '20 at 01:37
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    @Vincent How do you translate a slang like "geil" literally? I am reasonably sure without being an ethymologist that it comes from "geilen" which is plant-related (badly explained: when a plant shoots up after a rainfall), then turned into "geil" which means sexually arousing, then got used for awesome. – kutschkem Nov 05 '20 at 07:31
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    @kutschkem The original slang meaning was "horny", which later generalized to being "good/awesome", while keeping some of its unsavoriness. It's not excessively impolite, but 9/10 it is used by teenagers amongst themselves. Interestingly, some ad campaigns used it to buddy up to that demographic in the last few years, so I feel like it has lost a lot of its prominence and was surpassed by other slang terms. – Minix Nov 05 '20 at 16:06
  • This is the second self-contradictory phrase I've learned coming out of German: leider geil, and the better-known Schadenfreude. Now I'm curious if this is a common German phrasing, putting such opposites together? – Eiríkr Útlendi Nov 05 '20 at 18:17
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    "geil" can indeed be translated to "awesome", with even more of a connotation of "extremely satisfying" - be aware that it also has the meanings of "horny" and "nubile/handsome", and is considered far more of a colloquial/slang word in German than "awesome". The Deichkind lyrics play on that ambiguity also ... "Oh, Gott, wer ist diese Schrulle neben mir im Bett? Ich war wohl gestern Abend (leider geil)" – rackandboneman Nov 05 '20 at 18:24
  • @EiríkrÚtlendi This isn't really self contradictory, nor is Schadenfreude. Both situations just happen to combine a negative concept (unfortunately, misfortune) and an positive one (awesome, joy), but they are more unrelated than contradictory, and both can be expressed easily in English. Schadenfreude is a form of joy - nothing contradictory about it. It's just joy about an unfortunate event. – Kevin Keane Nov 05 '20 at 21:48
  • @EiríkrÚtlendi As rack says, Schadenfreude is not really a contradictio in adjecto: It would be if it were your own Schaden, but for some inexplicable reason it's always someone else's misfortune that elicits the joy. – Peter - Reinstate Monica Nov 06 '20 at 00:26
  • It seems my wording has led discussion astray. I'm not so interested in the stricter meanings of "self-contradiction". I'm more interested if this kind of "negative + positive" juxtaposition is a common construction. The two examples so far, leider geil and Schadenfreude, are both interesting and noteworthy because of this juxtaposition. How prevalent is this pattern? – Eiríkr Útlendi Nov 06 '20 at 00:29
  • @Minix The prime example for the "buddying up" (what a nice term) is probably a supermarket chain's viral video, "EDEKA Supergeil (feat. Friedrich Liechtenstein)". – Peter - Reinstate Monica Nov 06 '20 at 00:37
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    @EiríkrÚtlendi Ah, I see. Well, German philosophers, notably Hegel and Marx, were central to the development of modern dialectic ... who knows. Schadenfreude als Synthese... – Peter - Reinstate Monica Nov 06 '20 at 00:42