A photographer is suing Sir Rod Stewart for breach of copyright, claiming he used her image without permission.
Julia McLellan, from Hatfield Peverel, has lodged a claim of £9,999.99 against the singer at Chelmsford County Court.
She claims Sir Rod, 73, was not authorised to use a picture of him with a former girlfriend as a gig backdrop.
Sending the matter to trial, District Judge Stephen Hodges urged both parties to mediate as the case had "tears written all over it".
Mrs McLellan, 63, said she repeatedly asked Sir Rod's lawyers for a fee to cover the use of the image in 2015, but they refused.
She took action on behalf of McLellans agency, which she runs with her husband John, after efforts to settle the matter amicably failed.
The photograph in dispute dates from the 1960s and had never been published until it was used on a video backdrop at BBC2's Live in Hyde Park: A Festival in a Day concert.
It was taken by Sir Rod's former school friend, Christopher Southwood, but Mrs McLellan says she acquired the copyright in 2004.
She claims Mr Southwood gave Sir Rod a copy of the photograph as a keepsake but said: "That's very different from using it commercially."
In defence papers lodged with the court, Sir Rod's team argued the court should reject Mrs McLellan's claim for "an absurd level of damages for a totally innocent, brief and incidental use by Sir Rod of a personal snapshot as part of another, more substantial, artistic work".
Sir Rod, whose first number one album was "Every Picture Tells A Story", states the image was one of hundreds used and it appeared for only eight seconds.
Speaking after the hearing, Mrs McLellan said if she wins she will split the payout equally with Mr Southwood.
District Judge Stephen Hodges said: "In terms of the totality of Sir Rod's lifestyle, it's a modest claim.
"We cannot make people mediate but I will repeat the encouragement and request.
"Try and resolve this. I think this has got tears written all over it."
No date has been fixed for the next hearing.