Like for the list by stars recently mentioned (here), you can list by car year, though that you will get first all the cars without year, so it is a little difficult to find the page with the oldest cars (start from the middle of pages list, move by group of 50 pages, etc.)
Currently it is around page 169, but depending on what is identified or added to the site you may have to go to next pages if you see makes starting by "y" or "z", or go to previous pages if you see cars of the 1910s/1920s:
http://www.imcdb.org/search.php?resultsStyle=asList&sortBy=2&makeMatch=2&make=&modelMatch=- 1&model=&page=169
On the search page you can get the oldest movie, e.g. those made before 1910:
http://www.imcdb.org/movies.php?titleMatch=0&title=&yearMatch=2&year=1910&movieType=- -1