Hi,
Sorry to hear you're having problems with your boss's laptop.

Have you tried plugging in the WD external drive to a different working Windows computer? If it also fails to work on that 2nd test computer, it's likely that hard drive has failed. If it works on the 2nd computer and you can access the file, copy it, and even play it, the external drive may still be Ok, but your boss's laptop may have a problem.
Typical problems are:
1.) Virus/Malware infection
2.) Windows registry corruption
3.) Failing or failed internal bootdrive on the laptop
It's also a really good idea to test that external hard drive whether or not it works on a 2nd computer. I suggest this drive diagnostic from WD the makers of your boss's external drive available at this link here:
Link Removed.
It is important to note that WD has 2 different drive diagnostics they supply to end users for free,
(1.) WD Drive Utilities for Windows, and
(2.) Data Lifeguard Diagnostic for Windows. The link I gave you above is for the WD Drive Utilities for Windows, as the DLG (Data Lifeguard Diagnostic) doesn't work on most external usb drives. The DLG diagnostic is for internal bootdrives on desktop PCs and Laptops only and won't work on your boss's external drive!
Next, prior to running any other diagnostics or repair utilities on that WD external drive (besides the
WD Drive Utilities for Windows I provided you the link to), we suggest that you
MAKE CERTAIN YOU BACKED UP ALL THE PERSONAL DATA YOUR BOSS HAS ON THAT DRIVE TO EXTERNAL MEDIA BEFORE PROCEEDING FURTHER TO AVOID IRRETRIEVABLE DATA LOSS!!
To address the first 2 issues you can try the following:
1.) To check if your external drive has viruses, use whatever built-in Antivirus (AV) that is already installed on your boss's laptop, ensure it's up to date and has the latest definitions.
Scan/remove all viruses found. Next, download the Free antispyware
MALWAREBYTES program from
malwarebytes.org, and
scan/remove all spyware viruses found. Retest your file access from your boss's laptop. If it now works, you had a virus infection and removed it which fixed it!
2.) To repair Windows registry corruption, try these software repairs
(again, only run these repairs after you've backed up your boss's external drive and you've verbally verified that with him!).
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File scans
Right click on the Start menu icon and from the revealed list choose
'admin command prompt'. Type:
sfc /scannow
press enter and await results
In the same command prompt and after the above scan has finished type:
dism /online /cleanup-image /restorehealth
Press enter and await results (longer this time).
If the first scan found files it could not repair but the second scan is successful, run the first scan again using the same command prompt box and this time it should repair the files found.
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These repairs are to be done after doing Chkdsk repair first which you've already done. These 2 repair commands are excerpted from a recent post by
kemical, who is also helping you here on this thread, so they are safe to do once you've taken our recommended precautions discussed in paragraphs above. Remove the external hard drive from your boss's laptop and reboot it. Then once it's in Windows, reconnect the external drive to the laptop and retest your file access and try to play the file again. If it now works, you've fixed it!
These procedures and repairs will work on most laptops, probably about 85% of the time. Give these methods a try and it should take care of it. Of course, if none of these work, or the WD diagnostic shows that the drive has failed, you should purchase a new external drive for that laptop and get it working. Set aside the failed external drive, and take it to your local computer repair shop and pay them to get your boss's data off of it and put it into DVD discs, USB flash drive, or another new external hard drive and proceed from there.
Let us know how it goes.
<<<BIGBEARJEDI>>>