How do I shrink all files quickly for all databases? In SQL Server (2008 in this case) how can I quickly shrink all the files, both log and data, for all databases on an instance? I could go through SSMS and right click each and choose Tasks -> Shrink, but I'm looking for something faster.

I scripted some "Create database" scripts and forgot they had ballooned sizes for defaults, and don't need quite that much space reserved for these files on this project.
When you do "Tasks -> Shrink" from the GUI it actually issues a DBCC SHRINKDATABASE command behind the scenes. Try it. When the dialog box comes up, don't click the "OK" button. Instead, click the "Script" button. You'll see the command in a query window. Combine that with a query on sys.databases (leave out master and msdb), and you can make a script to shrink all of the databases.

For example (taken from jcolebrand's comment):

SELECT 
      'USE [' + d.name + N']' + CHAR(13) + CHAR(10) 
    + 'DBCC SHRINKFILE (N''' + mf.name + N''' , 0, TRUNCATEONLY)' 
    + CHAR(13) + CHAR(10) + CHAR(13) + CHAR(10) 
FROM 
         sys.master_files mf 
    JOIN sys.databases d 
        ON mf.database_id = d.database_id 
WHERE d.database_id &gt; 4;


Copy the output of that query and run it to shrink all your files.