Is it possible? Yes 
I always want to see information about computer name, memory, IP address etc. on my serevr desktop, so I'm using BGinfo for this purpose.
1. Download BGInfo, and copy it on your server 2008 CORE box.
2. Configure BGInfo and create template.
3. Create bat file that looks something like this one
c:BGInfoBGinfo.exe c:BGInfoTemplate.bgi /timer:0
4. start regedit by typing regedit in command prompt
5. Navigate to HKEY_CURRENT_USERSoftwareMicrosoftWindowsCurrentVersionRun
6. Create new string value named as you wish, and point it to previously created bat file
7. log off and log back on - you will have your background picture
Using similar procedure you could autostart Opera or Firefox browser
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