You are populating the Listbox with file names without extensions.
So in this line you need to append the extension again:
pictureBox1.Image = System.Drawing.Image.FromFile(@"C:/Users/Dan/ImgDirectory/" + listBox1.SelectedItem.ToString());
So it becomes this:
pictureBox1.Image = System.Drawing.Image.FromFile(@"C:/Users/Dan/ImgDirectory/" + listBox1.SelectedItem.ToString() + ".jpg");
As a side note, this sort of error can be easily detected if you use debug break points. Since that line was the one giving you trouble you should put a break point there and start debug (F5). When the code stops at that break point you can check the value of @"C:/Users/Dan/ImgDirectory/" + listBox1.SelectedItem.ToString())
and you would've found the problem.