This was the exact situation that Sussex-raised Angus Goldsmith found himself in when he had the chance to interview the legend himself at a recent charity event.
Angus, who is a
Youth Ambassador for childhood bereavement charity
Winston's Wish and grew up in West Sussex, interviewed the comedy king of the dancefloor as part of a
dedicated fundraising event supported by Bill following the deaths of close friends with children.
Angus, 25, became involved with Winston's Wish after his mother died following a road cycle accident when he was 21:
"My mum died a few years ago following a traffic incident. I was home for Easter with my mum and she was going for a cycle ride which she routinely did and she really wanted me to come but I had some writing up to do for University.
"Basically, she ended up in an accident and the next week was a bit of a blur. Over the next few months she didn't really show any signs of improvement and in July the following year we decided it was in her best interests to withdraw life support. With all these experiences, I am still trying to figure it all out."
Prior to becoming involved with
Winston's Wish, Angus grew up watching Bill Bailey with his elder brother:
"My brother had Black Books on DVD and I have vivid memories of sitting down and watching it with him.
"I was probably too young to appreciate much of the humour, but it's still very visually funny.
"I've also seen Bill on QI and Never Mind the Buzzcocks - two shows I enjoy and admire.
"I was taken aback meeting him - he's in the 'national treasure' category surely!"
Bill Bailey recently performed a comedy evening in aid of Winston's Wish which
raised an impressive £45,856.48.
It was before the show that Angus sat down to interview Bill about his own experiences of grief after his own mother and close friend and fellow comedian Sean Lock died.
Angus explains:
"Initially, I opened up about my experience of bereavement and I could see Bill instantly relax into the conversation, then when he started talking about his bereavement, I also relaxed into the conversation.
"I think my initially mentioning it opened that doorway of permission for us to both be open about our experiences.
"We were there as a result of bereavement in one way or another. Talking about it generated a sort of common ground.
"I think it's valuable to be open about feelings. Articulating our feelings helps us better understand them - when we understand our feelings we're better able to manage and react to them.
"It's not always easy to be open though, so I think we each need to find and practice our ways of doing so.
"My involvement with Winston's Wish was like Bill said in the interview, I can't control this situation, but I can control to a degree the aftermath and it was always very important for me to make some good from the situation and create some good that wouldn't have happened."
Angus explained that he still has to cope with different emotions and triggers for his grief:
"A couple of days ago I was thinking about what I was going to wear for the interview with Bill and I actually went to go and text my mum and I just had this brief moment, and everything just got to me. It was quite bizarre.
"I often stumble across old photos or memories and think 'Wow, that was what life was like back then'.
"It acts as a benchmark to see how far I've come and how much things have changed - it's a reality check.
"Looking back on the more difficult moments, I'm in admiration of my younger self for withstanding them and coming out the other end a more resilient and sensitive person.
"The difficult moments are obviously difficult, but we learn from them and I believe they make us more emotionally aware and sensitive individuals."
Growing up in West Sussex, Angus shares how a special area near where he grew up still holds precious memories of his Mum:
"We grew up in Hurstpierpoint, a village just the other side of the South Downs from Brighton. Wolstonbury Hill was a regular walking spot we visited whilst growing up.
"It became my regular stomping ground for my runs, my parents and brother would frequently cycle around it as part of a larger bicycle loop across the Downs and we also walked the dog up there frequently. It holds a lot of sentiment for the whole family.
"We had a stile installed by a voluntary group of retired individuals who build and maintain highly accessible stiles and other wooden structures on public rights-of-way.
"My dad discovered them when he moved to Sussex before I was born - you can't venture out into the Sussex countryside without seeing some of their work.
"They do work all around the county and they have a little notice on each of their structures informing users who installed the feature. We thought this would be very fitting for Mum - a stile on our favourite hill."
Winston's Wish is keen to reassure bereaved young people and their families that they are welcome to chat online, email or call for free to speak to a bereavement support worker by calling 08088 020 021, emailing ask@winstonswish.org or using the live chat at http://ask@winstonswish.org.