Michael Bublé: My initial suggestion is Crazy Love and To Be Loved. Those are the most easily accessible albums in my personal opinion, especially for people that are coming from the pop genre. Call Me Irresponsible and It's Time should be your next step. If you are already comfortable with the big band, blue-eyed jazz sound, then I suggest giving his self-titled debut a fair listen and Come Fly with Me.
B'Day. That album represents who she is and her personality the most. Also, most of the songs on it are growers so if you can listen to and enjoy that, you'll pretty much enjoy any song she puts out.