Nope. Outlook Express cannot do that.

Signature
Jim Pickering, MVP-Outlook Express
Please reply only to newsgroup.
Jim,
Here is an enlightening dialog on the subject from Michael Jennings:
----- Original Message -----
From: "Michael Jennings" <harvest@way.invalid>
Newsgroups: microsoft.public.windows.inetexplorer.ie6_outlookexpress
Sent: Tuesday, March 30, 2004 1:28 PM
Subject: Re: how to print a bunch of emails with one command?
If I drag a file from OE to the printer icon I get
the do not enter (/) - not the plus [+] sign.
It is the same for several files as for one.
If I move OE files to a windows folder and
drag an eml or nws file to the printer icon I get
"This file cannot be printed. Please try opening the file
with the correct application and printing from there."
It is the same for several files as for one.
On the other hand, if I select several txt or doc files
and drop them on the printer Windows says,
"You are trying to print multiple files at once.
Are you sure you want to do this?"
and my OK gets several files printed.
This won't work with a non-default printer.
If I rename eml and/or nws files *.txt the batch will
print, each as source - headers and all. A command
prompt is convenient for wholesale renaming.
If, inside OE, I select one file and ctrl-P it prints.
If, inside OE, I select several files and ctrl-P
only one of the files prints. Probably Office's Outlook
would print a batch of nws or eml - I could check.
Nope. Outlook Express cannot do that.
--
Jim Pickering, MVP-Outlook Express
Please reply only to newsgroup.
> I'd like to print a few dozen emails from a particular folder -- is there
> a
> way to that without doing each one individually and separately?
>
> Jack
Jim Pickering - 31 Mar 2004 18:06 GMT
There is one way to do what you have in mind, but you have to look at the
results and see if it truly serves your needs.
Highlight the messages you wish to print (using the Ctrl key to select
multiple messages), then click Message/Combine and Decode and on the
resultant combined message, use File/Print. See if that result is
acceptable.

Signature
Jim Pickering, MVP-Outlook Express
Please reply only to newsgroup.
> Jim,
>
[quoted text clipped - 42 lines]
>>
>> Jack