There was such a time. Same as with Google. Interestingly, around 2015-2016 both companies significantly shifted to iterative products from big innovations. It's more visible with Google than Apple, but here's both.

Apple:

- Final Cut Pro

- 1998: iMac

- 1999: iBook G3 (father of all MacBooks)

- 2000: Power Mac G4 Cube (the early grandparent of the Mac Mini form factor), Mac OS X

- 2001: iPod, iTunes

- 2002: Xserve (rackable servers)

- 2003: Iterative products only

- 2004: iWork Suite, Garage Band

- 2005: iPod Nano, Mac mini

- 2006: Intel Macs, Boot Camp

- 2007: iPhone and Apple TV

- 2008: MacBook Air, iPhone 3G

- 2009: iPhone 3Gs, all-in-one iMac

- 2010: iPad, iPhone 4

- 2011: Final Cut Pro X

- 2012: Retina displays, iBooks Author

- 2013: iWork for iCloud

- 2014: Swift

- 2015: Apple Watch, Apple Music

- 2016: Iterative products only

- 2017: Iterative products mainly, plus ARKit

- 2018: Iterative products only

- 2019: Apple TV +, Apple Arcade

- 2020: M1

- 2021: Iterative products only

- 2022: Iterative products only

- 2023: Apple Vision Pro

Google:

- 1998: Google Search

- 2000: AdWords (this is where it all started going wrong, lol)

- 2001: Google Images Search

- 2002: Google News

- 2003: Google AdSense

- 2004: Gmail, Google Books, Google Scholar

- 2005: Google Maps, Google Earth, Google Talk, Google Reader

- 2006: Google Calendar, Google Docs, Google Sheets, YouTube bought this year

- 2007: Street View, G Suite

- 2008: Google Chrome, Android 1.0

- 2009: Google Voice, Google Wave (early Docs if I recall correctly)

- 2010: Google Nexus One, Google TV

- 2012: Google Drive

- 2013: Chromecast

- 2014: Android Wear, Android Auto, Google Cardboard, Nexus 6, Google Fit

- 2015: Google Photos

- 2016: Google Assistant, Google Home

- 2017: Mainly iterative products only, Google Lens announced but it never rolled out really

- 2018: Iterative products only

- 2019: Iterative products only

- 2020: Iterative products only, and some rebrands (Talk->Chat, etc)

- 2021: Iterative products only, and Tensor Chip

- 2022: Iterative products only

- 2023: Iterative products only, and Bard (half-baked).

The Next Cube being a very obvious inspiration here.

Mac OS X was a needed step, and entire books have been written about its creation. While it has some innovative pieces, it was very much a do or die situation for Apple, not brought on by innovation so much as the need to survive. (I'm sure BeOS fans will argue that BeOS was the real innovative OS. ;) )

> - 2001: iPod, iTunes

iPod was a, very well done, refinement of the existing MP3 device category. iTunes' innovation was the licensing deal they got with record companies, that is what really surprised everyone.

> - 2002: Xserve (rackable servers)

Not sure how this is an innovation? Rack mount servers had been around a long time.

> - 2004: iWork Suite,

Microsoft literally had a product called Microsoft Works that was originally released in 1988 and came shipped on tons of home PCs.

> - 2005: iPod Nano, Mac mini

The iPod Nano was cool, the Mac mini was a wonderful feat of engineering and cost reductions.

> - 2006: Intel Macs, Boot Camp

Necessity brought this about.

> - 2007: iPhone and Apple TV

This is a perfect example of Apple entering an existing product category and doing an amazing job of execution. Palm, Blackberry, and Microsoft were already releasing very capable smart phones, but none of them bothered polishing the product (MS and Blackberry focused on corporate sales, end user experience was not the top priority) and while Apple did push a lot of technology forward to make the iPhone (notably screen tech and using capacitive touch screens), their main innovation was realizing they could get customers to pay for a cell phone. For those who don't remember, prior to the iPhone, most customers got their cellphone for "free" from their cellular provider in return for agreeing to a 2 year contract. Apple realized if they made a really nice product, that people would buy it.

Apple also did some really cool, and now largely forgotten about, positioning here involving the iPod Touch, where the iPod Touch had access to the full App Store and became entry level "kids toy" devices that got people into the ecosystem.

Heck arguably the App Store was a larger innovation than the phone.

Fun fact: Microsoft had an App Store ready to launch for Windows Mobile (pre Windows Phone 7) but it was scrapped at the last minute because an exec thought that "no way would phone users ever pay for apps".

(When I joined MS in 2006 the source code was still laying around in the Windows Mobile source tree!)

Apple TV was arguably too early at this point in time, I'd say it didn't really take off until later generations when more streaming media was available.

But innovative? Web TV was out in the late 90s (!!) and Microsoft tried to do Media Center PC's since 2002. Heck for awhile with Xbox 360, Microsoft basically owned the "TV smart device" market segment. (and they released the Xbox One as a media streaming device and sort of forgot that it was also a games console... oops)

As with most products, Apple just did a really good job of it, but Roku has dramatically outplayed everyone else in the market by getting embedded directly into cheap TVs sold at Costco.

> - 2010: iPad, iPhone 4

iPad is/was an amazing product, and it succeeded thanks to great apps.

It was also a refinement of Tablet PCs which have been around since the late 80s/early 90s.

Apple was willing to do what Microsoft wasn't, break all back-compat and make a really good single purpose device. Microsoft's tablets (some of which are really damn nice!) were always hamstrung because Microsoft never could go all in on abandoning existing x86 software. (The closest attempt being Windows 8 RT, which managed to make the perfect set of compromises to anger everyone!)

> - 2015: Apple Watch, Apple Music

The first generation Apple Watch was... meh. Now, I say this as someone who was working on a direct competitor - I am still not sure how it has such a miserable battery life and why such a massively overpowered CPU and GPU still dropped frames.

I am not sure what is innovative about Apple Music, vs every other streaming music service.