To find the exact values of tan 165 and tan 285, using the identities tan x = sin x / cos x is essential. The discussion highlights the importance of calculating sin 165 and cos 165 accurately to derive tan 165. A suggested method involves using the angle subtraction formula, specifically tan(pi/3 - pi/4). Participants emphasize that there are multiple representations for the exact value of tan 165, and verifying these against textbook answers is crucial. Overall, understanding the relationships between sine, cosine, and tangent is key to solving these problems accurately.