When you click Photo Library, you’ll be asked to choose a set of photos to be used for the screensaver. You can click individual photos, Moment, Collection, Place, Year, Face, Album or Shared iCloud album. Tick off the Shuffle slide order box if you want the screensaver to cycle through your chosen photos in random order. This photo slideshow maker offers a sizable library of professional-looking transitions, backgrounds, and effects to help professional photographers showcase images and videos in modern fashion. This photo slideshow maker pops up the ProShow Wizard when you open it to help inexperienced users make a slideshow. Extensive options for creation. The 'Shuffle slides' option can be turned on to randomize the order of all slides in a deck. The order is randomized each time the presentation loads. Note that we never shuffle decks while you're in the editor.

Photo
There are two ways to have a slideshow in iPhoto. From within an album, you can click the Play button and get a quick slideshow. With this method, you have the option to shuffle the order, and play music -- but you can't 'fit' the duration of the slideshow to the music.
The other way is to create a slideshow in the sidebar. Here you have the option of setting the duration of each slide to match that of the music (in my case, I had a 20 minute montage), but there is no way to randomize the order -- you have to drag by hand to set the manual order.
My idea is to title the photos with a random number, then sort by title, thereby randomizing the images. Run this AppleScript in Script Editor to do just that: Note: This solution assumes that you have created a separate iPhoto (v7) library for the slideshow, as it re-titles all the images in the library. It is easy to change this to only randomize a specific album; just change the album name in the script from photos to the album name.
After running the script, select Choose View » sort by » Title in the menu. Then select all, and create a new slideshow in the sidebar. Its order will be randomized.
[robg adds: I modified the script to add the comments and comment out the tell album line. To use the script, please follow the instructions to provide an album name and remove the tell album... line's comment marker. I did it this way because this script will re-title your images, and I didn't want anyone accidentally overwriting their laboriously-applied image titles in their main library. Creating a separate slideshow-only library is the best solution; iPhoto's help explains how to create a new library if you're not familiar with the process.]

It’s absolutely frustrating when you set out on a task that seems like it should work, and then wind up wondering if it’s your fault. This is the case with Photos 3.0 for macOS and its broken workflow for creating slideshows: it sorts images and videos in random order.

Macworld reader Marie is one of the people who cannot figure out what’s going wrong. She asks, rightly in all caps, “HOW CAN I GET MY SLIDESHOW PHOTOS IN THE ORDER I WANT THEM?”

In previous releases and in iPhoto, you’d follow these steps:

  1. Select some items or have no items selected while viewing a regular or smart album to select the whole album.
  2. Create a slideshow. In Photos, that’s File > Create > Slideshow. An entry is created in the Projects list with the name you choose.
  3. And, hurray, the pictures and movies would be referenced in a slideshow view in the order they appeared in the album.

Shuffle Photos Slideshow Mac

Photos 3.0 inexplicably broke this arrangement, and it’s remained broken since its introduction in High Sierra in 2017. Until Apple fixes this issue—perhaps in the release of Photos with the upcoming Mojave?—you have a few workarounds, none of which are quite as ideal, but all of which retain the order in which you organized your media. (Update: Mojave didn’t fix it, either.)

Manually sort the slideshow. After creating a slideshow, you can use the thumbnails at the bottom to re-arrange media into the order you want. This is tedious and unnecessary, but lets you use all the slideshow features.

Windows 10 background slideshow shuffle

Use the Slideshow feature in any view. This feature isn’t always apparent, but you can create an ad hoc slideshow by selecting any set of images in any view and Control-clicking. Then select Play Slideshow. In an album, you can also click the Slideshow link at top. You don’t get all the controls and options in a separate slideshow Project, but you can pick a theme and music.

Use iMovie. While it’s convenient and fast to create a slideshow within Photos, you can have more options and avoid the need to re-arrange images and videos by using iMovie, which preserves the sort order in your albums when you import. It could be overkill, but you can get by with the basics or push up the pizzazz factor, then export as a movie. (iMovie in the App Store.)

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Shuffle photo order for slideshow machines

Photo Shuffle Slideshow

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Windows 10 Background Slideshow Shuffle

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How Do You Shuffle Photos In Slideshow On Mac

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Shuffle Photo Order For Slideshow Machine

Glenn Fleishman is the author of dozens of books. His most recent include Take Control of Your M-Series Mac, Take Control of Securing Your Mac, Take Control of Zoom, and Six Centuries of Type and Printing. In his spare time, he makes Tiny Type Museums. He’s a senior contributor to Macworld, where he writes Mac 911.