It is the first brand-led promotion to launch on the show and will run every weekday morning from January 30, tying in with the new series that will broadcast over five nights that week on Channel 4's digital channel E4.
The promotion will involve O'Connell, who joined Virgin on Monday, crossing over live to '"Brian the Monkey" every morning, who will perform and fail his own dangerous stunts.
Listeners are invited to call in and guess whether he is going to survive the stunt such as Russian Roulette for a chance to win one of five "risky" holiday prizes each day.
Holidays include: bungee-jumping in Australia; swimming with sharks in Scotland; wing-walking on an aircraft at 100mph: skydiving over Belgium; or Zorbing -- that is, being put in a rubber ball and rolled down a mountain -- in the Austrian Alps.
On the E4 show, viewers will see an escapologist hanging and burying himself alive as well as a stuntman turning himself into a human firework. The programme is deemed so dangerous that it is being broadcast with a short time delay in case anything goes wrong.
John Walker, head of radio planning and buying at OMD UK, said: "Virgin Radio delivers exactly the right national audience we need to engage with and encourage to tune into 'Death Wish Live!' that evening.
"The massive comedy appeal of Christian and 'Brian the Monkey' combined with the great prizes up for grabs will really connect with the audience."
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