Jensen Ackles’ Hilarious ’90s Modeling Photos Revealed

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Few people who achieve fame in the entertainment world can trace their first paid job to the origins of their successful careers. In simpler terms, everyone has humble beginnings, even well-known figures such as Jensen Ackles, known for his roles in ‘Supernatural’ and ‘The Boys’. His initial steps into stardom were gradual, marked by his teenage foray into modeling, which brought out some amusing expressions that made quite an impression when pictures surfaced on ‘The Tonight Show’!

What Happened When Jensen Ackles’ Old Modeling Pics Were Shown On The Tonight Show?

Many accomplished actors and gifted individuals may have regretted some early endeavors they undertook to kick-start their careers and earn money, which they’d prefer remained hidden due to potential embarrassment. However, in this digital era where virtually everything can be uploaded and preserved indefinitely, it seems unlikely that such projects will vanish from public view in numerous instances.

Jensen Ackles, who recently finished filming a reunion for Supernatural with his co-stars Jared Padalecki and Misha Collins for the upcoming fifth and final season of The Boys, experienced an unexpected discovery. During a visit to The Tonight Show Starring Jimmy Fallon to promote his new series, Countdown, which will air in 2025 (and can be streamed with an Amazon Prime subscription), Ackles was taken aback when the host revealed details about his early modeling days as a ’90s teen model. Initially puzzled by the mention of a “modeling career” (as evidenced in the picture at the top of this article), Ackles was then confronted with the truth about his past work for the JC Penney catalog.

Gosh, does he seem embarrassed or not? It’s interesting to note that this situation isn’t as dire as it could have been for this segment. Perhaps he could have saved his dejected expression for a more appropriate time. As it stands, discovering that he was caught smiling and grooving to ’90s music (and I can’t help but imagine he’s jamming to Vanilla Ice) at around 13 to 14 years old isn’t all that damaging. At least he earned some money from it, right? However, the embarrassment didn’t end there:

Wow, it seems this individual has reached the zenith of awkwardness with their fashion choices. It’s common for those who lived through different fashion eras to cringe at some of the styles, whether they wore them themselves or had them imposed upon them. In this instance, even though the former Days of Our Lives actor was dressing for work, it doesn’t make the outfit any better. And yes, if you’d like a closer inspection, I’ll happily provide one.

It seems like he’s biting into a popsicle in this picture, which I find unusual for real people. However, young Ackles looks quite blank and confused in this photo, so perhaps there’s more to it. I can’t help but question if this is indeed his way of eating popsicles, though that’s a subject for another discussion. In any case, this individual would undoubtedly be the target of Dean’s mockery, regardless of age. Here’s another photo, and trust me, it’s one for the books. Check it out:

It seems like this is the least awkward image, but with a twinkle in his eye, he’s fully participating. Interestingly, he claims to have deliberately imitated the character Joey Tribbiani from Friends, as he considers it his version of the “How you doin’?” look. There’s nothing more distinctly ’90s than that.

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2025-06-25 23:40