For the movie thing! William Shatner, Bellamy Young, David Tennant, Zoey Saldana, and Michael B Jordan!
I had a LOT of trouble figuring out what I'd do with this. The concept is still pretty loose, so just humor me.
Young plays Andrea, a widowed mother. After her husband's unexpected death, she found herself lost. Adrift. Two years later, she's ready to pursue the dream she gave up at a young age: Singing. The problem? Most people aren't eager to welcome a nearly fifty year old woman to the music scene.
Enter Bradly, played by Shatner. He's been in the music business since he was 15 years old, and now, he's willing to be Andrea's manager, to take a chance on her when no one else will. But why? What isn't he telling her?
Jordan plays Drake, a singer at the height of his career. He ends up mentoring Andrea, teaching her the ups and downs of the music industry. (It's a little weird for both of them, since he's technically young enough to be her son, but he's definitely the expert here.)
Saldana plays Andrea's best friend, Lily, who pushes her to take the leap. She's been involved in the music industry for years, mostly working as a secretary here and there, but her dream is to be a professional song-writer. Andrea offers her a deal: I'll sing, if you write me something TO sing.
Tennant plays Andrea's ex boyfriend, Samuel. She honestly expected to marry him, until he broke things off suddenly without warning. Now Bradly wants him to be her publicity agent. Andrea is less than thrilled, but determined to make this career work.
Drake and Lily would also definitely have some sort of romance, probably of the "secret- find out 3/4th of the way through the movie" variety.