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Brits say "dar-bee" for both the town and the race, but Americans pronounce it as it's spelled.

Did Brits used to say "der-bee" too and that's why it's spelled that way but they changed over time?

Was it always pronounced like in the UK but American pronunciation followed the spelling for some odd reason?

Is it borrowed from some other language so there's a disconnect between the spelling and the UK pronunciation?

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The pronunciation came about because of the famous British inland pirate. When asked what he's looking for inland, he said "Dar be treasure". –  Mike Brown May 15 '12 at 0:31
    
It's not that neatly divided. Some areas of Britain say darbee, some say derbee. Australians and New Zealanders are similarly split. Personally I pronounce it both ways at random, sometimes in the same sentence. –  Optimal Cynic May 15 '12 at 1:57
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People in Derby say "Der bee" –  mgb May 15 '12 at 4:21
    
Is something similar going on with the name "Berkeley", often pronounced "barklee"? –  Mark Dominus May 15 '12 at 17:05
    
I have never heard a brit say der-bee. FWIW I used to live on the Derbyshire/Yorkshire border. Oh and yes, I never even thought about it, but the same thing does happen with Berkeley: www.youtube.com/watch?v=xTeiYN_Vq6E –  Gareth Simpson May 15 '12 at 18:27
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1 Answer

This website says

It's the result of the same process (that is, erroneous pronunciation) whereby "learn" becomes "larn" in some (very) nonstandard American dialects. One feature of uneducated speech in England around the 1800's was a tendency to pronounce the "er" sound of words like "clerk" as the "ar" sound of "clark". The phenomenon was sufficiently widespread that the English novelist Henry Fielding used pronunciations like "sarvis" for "service", "sartain" for "certain", and "parson" for "person" in the speech of characters meant to seem vulgar or unintelligent. Due to the overwhelming influence of such people in England (that is, the uneducated), these previously unacceptable pronunciations eventually became standard for some words, like Derby, Berkeley, and clerk...
Source(s): J.C. Wells, Accents of English

So a more general sound change that took "er" to "ar" was present in some lower-class British accents when Henry Fielding wrote Tom Jones (ca. 1750). This 1849 dictionary found in Google books indicates that this pronunciation had for the most part vanished a hundred years later1. The pronunciation now persists in only a handful of words:

Berkeley, clerk, derby, Hertfordshire, sergeant, varsity.

I take the liberty of including varsity here because it was originally short for university. However, university has reverted to the standard pronunciation, while varsity has switched to the phonetic spelling.

1 Interestingly, the dictionary also says that many Americans pronounced sergeant with "er".

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I’ve sure never heard sergeant with “er” rather than “ar”; I take it neither have you? The rest is certainly fascinating. –  tchrist May 17 '12 at 0:33
    
I've never heard sergeant with "er" rather than "ar", either. I assume this pronunciation died out somewhere between 1850 and now. –  Peter Shor May 17 '12 at 9:42
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