Has anyone dealt with a music supervisor getting bigger songs?

What do you mean by "bigger"? If you mean famous songs, I recommend you not go that route. Famous songs, unless in the public domain, are going to be INSANE AMOUNTS OF MONEY.
 
What do you need help with? If you are talking to a Music Supervisor then that's the person who is helping you. Right?? Any question you ask us could better be answered by them.
 
From Wikipedia:

A music supervisor is somebody with a broad and encyclopedic music expertise and a sophisticated knowledge of music licensing and negotiation. Typically, a music supervisor proposes previously recorded songs to the director or producer of a film, advertisement, television show, trailer, promo, video game, or any other form of visual media. A music supervisor will usually act as a liaison between the creative and business ends of the process......

A supervisor’s responsibilities are to locate, secure and oversee music related talent. They liaise between the rights holders of the recorded music involved and the director of the project they have been hired to work on. In addition, they advise, generate and work within financial parameters of the project they are hired to work on. They must deliver musical elements within a timely manner and secure legal rights of the song before it is used. The music supervisor will gather the appropriate information to list credits and, in certain cases, will manage royalty collection.
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So your music supervisor is supposed to advise you on how to obtain the "bigger" songs you desire; that's why you hired them in the first place!!!!!!!! If your music supervisor cannot do this than s/he is not as qualified as they claimed to be.

"Big" or famous songs are pricy. As I have mentioned, "The Middle" by Jimmy Eats World goes for $100,000 plus points; "Come Go With Me" by the Del Vikings goes for about $25,000 plus points (these numbers are from personal knowledge). You will notice that you almost never hear original recordings of Beatles songs in films; hearsay has it at $500,000 to $750,000 per track plus a very large points requirement.
 
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