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There is a nice Thinkpad configuration utility (http://tpctl.sourceforge.net/configure-thinkpad.html) for GNOME based on tpctl.
IBM Thinkpad R50e
MSa: Ubuntu 5.04 works well; all hardware, except for the Winmodem, is fully supported out-the-box.
IBM Thinkpad T23
Anon: I have installed Gentoo Linux on a T23 with very few problems. Sound (with ALSA) 'just works', as does ethernet and all the basics (save WinModem, which I have not tried). There are a few Thinkpad-specfic packages in portage that might be useful for any Thinkpad model: tpb (http://www.nongnu.org/tpb/) (Thinkpad buttons utility), thinkpad (Thinkpad system control kernel modules), and ibm-acpi (http://ibm-acpi.sourceforge.net/) for IBM ACPI extras.
IBM Thinkpad 380ZD
Anon: I have installed Mandrake 8.1 on this 1998 Pentium 233 laptop at work, which dual boots with Windows 98. No problem on the intallation and all hardware was automatically recognised - the network connection to the net was hassle free. In fact the installation was much easier than configuring Windows 98, which involved downloading a number of drivers and patches from the IBM site.