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Old DSLR lenses can be enjoyable to use. They've got imperfections that you don't see in most modern lenses. Plus, they really make you work for the shot. In a world where photography is so simple, they're refreshing. But in the past 10 years, lots of manufacturers have only cared about clinical perfection. This has surely satisfied tons of different photographers who wanted to get it all finalized in post-production. So what lenses are worth buying? And who should buy those lenses?
This is the era when suddenly, lens manufacturing really started to step up. It was ushered in by the Sigma Art lens lineup and the Zeiss Otus lineup. Almost overnight, third-party lens manufacturers started making viable lenses for lots of photographers who wanted clinical perfection. The Zeiss Otus lineup was considered a "No compromise" lens lineup. But the prices were exorbitant, and the lenses lacked weather sealing. Eventually, they were outdone by a bunch of other options on the market.
In 2021, when I'm writing this article, we're still in a pretty clinical spot. But there's evidence that brands are starting to change their tune. Canon RF glass isn't super clinically perfect though it has a beautiful look to it. Leica is similar. Sony obsesses over clinical perfection. Manufacturers have effectively killed the fisheye look and distortion at wide angles. That's a good thing in some ways. But at the same time, they're killing the soul and charm that some of those other lenses had.
If the clinical look is what you want, then this era is great for you. More importantly to us, this is also when weather sealing really started to be taken seriously.
The years 2000-2011 were arguably a sweet spot. Lenses from this time often still had a bit of imperfection but also were leaning more towards the clinical look. Canon made some wonderful old DSLR lenses at this time, as did Nikon and Leica. This was an era where Tamron and Sigma were arguably a joke to many photographers. But the German and European brands were making some fantastic glass during this time. The old Leica and Zeiss manual focus lenses were beautiful from this era. I remember my first time working with some Zeiss lenses. I easily fell in love. Photographers like Jeff Ascough and Chris Weeks were constantly in the feeds talking about these kinds of lenses.
For the record, Sony was still working with the Minolta A mount, which later became the Sony A-mount. Those lenses are okay but not spectacular. The exception is Sony's 135mm f1.8 that they made with Zeiss. This lens has far more character and a less clinical look than the modern version.
As far as build quality goes, this is a typical era that required a UV filter on the lens to complete weather sealing.
Lenses from this era were arguably in a weird spot. I've used tons and tons of lenses. But I can't think of any except for Leica lenses that really stand out from this time. Canon EF mount had a few L primes like their 35mm f1.4 L. This was a very transitional era for lots of brands. Autofocus motors and electronics were really, majorly becoming the norm as brands moved away from major manual controls.
Photography in the 1990s is fascinating. The majority of it is on film. Lots of photos were done using a fisheye lens that gave it a very iconic look. Yet, lots of work was also done on medium format film. Personally speaking, some of my best photos early on in my career were made with the first version of the Canon 35mm f1.4 L. That lens was made in 1998. Think of this time as the peak film era: great image quality for film, but still not clinically perfect and soulless the way digital is. By all means, don't even think about this era as having old DSLR lenses. But the lenses made during this time could easily mount onto DSLRs.
Lenses before 1990 are often what really wins my heart. This is when you're going to find all the really funky things. Weird lens flares, a bit of color fringing, sharp lenses without lots of contrast, and more dominant this time. You'll find it primarily with first-party manufacturers like Minolta, Nikon, Canon, Olympus, Contax, Bronica, and a few others. Leica, Zeiss, and Voigtlander also made beautiful lenses too! The image quality from those times is far and away different from what we see today. There are tons of great lenses to check out from the 1970s and more. Lots also happened in the world, so Zeiss lenses could be made in West or East Germany.