What you are after is a CROSSTAB Query. That only exists in some databases like Access but not in MySQL. However there is a way to simulate one in MySQL:
SELECT user_id, user_name,
SUM(IF(item_type='book', 1,0)) as book_count,
SUM(IF(item_type='journal', 1,0)) as journal_count,
SUM(IF(item_type='dvd', 1,0)) as dvd_count
FROM users INNER JOIN checkout USING(user_id);
Have a google for crosstab queries and pivot tables to see what is possible with different platforms.