Derek Webb, a Previous Dove Award Winner, Attends 2023 Show Sporting a Dress

Ex-Caedmon’s Call singer shares pre-show shot with drag performer ‘Flamey Grant’

Derek Webb apparently really enjoys wearing dresses.

So much so, in fact, the former Caedmon’s Call singer decided he would wear one to the Dove Awards, the biggest night in Christian contemporary music (CCM) — and invite a drag performer to join him.

While Webb is no stranger to the Dove Awards, with 10 nominations and three wins, he said this year would be the first time he attended in person.

Webb shared an image of himself wearing a woman’s dress, pearls, and black stockings with the caption, “despite having won a few over the past 20+ years, tonight will be my first ever trip to the dove awards, in the company of some very good friends (@FlamyGrant and @gracebaldridge, among others). i hardly ever dress up, but this feels like a very special occasion”.

despite having won a few over the past 20+ years, tonight will be my first ever trip to the dove awards, in the company of some very good friends (@FlamyGrant and @gracebaldridge, among others).

i hardly ever dress up, but this feels like a very special occasion. pic.twitter.com/BgWLSgnPm9

— Derek Webb (@derekwebb) October 17, 2023

A short time later, he tweeted another image of himself along with Matthew Blake, a former worship leader who wears makeup and women’s clothing and performs under the name Flamy Grant, and Grace Baldridge, who performs as “Semler.”

54th annual dove awards, here we come. pic.twitter.com/USPiTnIT5n

— Derek Webb (@derekwebb) October 17, 2023

Webb’s ex-wife, artist Sandra McCracken, was nominated at this year’s Dove Awards for her album Light in the Canyon. In 2014, Webb and McCracken divorced after 13 years of marriage after he admitted to an extramarital affair. The duo has two children together.

While Webb attributed his wardrobe to the “special occasion” of the Dove Awards, the “Jesus Hypothesis” singer hasn’t shied away from wearing women’s clothing on multiple occasions in recent months. 

On the same day as the Dove Awards photos, he posted another image of him in the very same dress in an anniversary message to wife Abbie Parker.

Earlier this week, he also promoted print-on-demand merch including a cup with an image of Webb wearing – you guessed it – a white skirt, along with the lyrics, “but I say unto you, you’re beautiful & free” from the song “God in Drag.”

In the Gospels, Jesus repeatedly used the phrase “But I say unto you” to proclaim Himself as a higher authority than the scribes, according to Got Questions.

When asked about his intentions in attending the Dove Awards despite not being nominated, Blake said he sees the appearance as “a sort of banner-wielding, exploratory scouting expedition.”

“We’re not going to stir up trouble or demand a single thing,” he told Baptist News Global earlier this month. “We’re simply going to be present, to express our queer joy, and to celebrate in our little corner of the room.”

Blake said he hopes to make “queer Christians” more visible simply by showing up at the Dove Awards.

“I am interested in representation and taking up space and providing an option for Christians who believe in a God that redeems the whole world, not just the heteronormative parts of it,” he was quoted as saying.

Webb and Blake made headlines earlier this year when the male pair both donned makeup, colorful wigs and women’s clothing while standing in front of a cross for a music video.

The video for  “Boys Will Be Girls” includes the lyrics, “I heard Jesus loved and spent his life with those who /Were abandoned by proud and fearful men /So if a church won’t celebrate and love you /They’re believing lies that can’t save you or them /Cause you’re so beautiful by any name.”

He also wrote a song titled “God in Drag,” in which he appears to mock the biblical notions of Heaven and Hell:

“You’ve heard it said /Oh, God so loves but he’ll reject you /If you so choose he will respect you /And for all time, he’ll disconnect you /From his love and those who’ve left you /And in the skies live on without you /While the devil’s flames surround you /In the place that he designed to /For eternity remind you /Of the choice that’s now behind you /Either way, I bet you’ll break a sweat.”

In a July interview with Sojourners, Webb said he wrote the song “for a dear person in my life who came out to [him] just a few years ago” and compared performing in drag for the “Boys Will Be Girls” video to the Incarnation of Christ.

“There is something about the experience of being put in drag by Flamy Grant that did feel incarnational to me,” he was quoted as saying. “And I think that’s a great analog to the work that Jesus did, and the power that incarnational risk has.”

The Dove Awards are set to air on TBN Oct. 20.

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