With a single client (Tidwell) and a single assistant (Dorothy Boyd, played by Renee Zellweger), Maguire seems washed up, but all 3 of them are determined to make it work. And, of course, they do. But this is more than the usual love-against-the-odds, anti-corporate-greed story. Renee Zellweger is genuinely moving as Dorothy, Jonathan Lipnicki is great (and never annoying, unlike many child actors) as her young son, and Cruise's familiar cocky smiles are at least in keeping with his character. (He has plenty to be cocky about, of course, being the world's most popular actor. But generally he's better in serious films like Magnolia.)
Cameron Crowe, who hasn't directed anything else this good since, has produced a long (but not over-long) and emotionally rich romantic comedy.